Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL
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1 Photoredox-Catalyzed Intramolecular Difluoromethylation of -Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H Containing 2- Azaspiro[4.5]deca-6,9-diene-3,8-diones. Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL Supporting Information Table of Contents I, General information (S2) II, Characterization of starting materials (S3-S9) III, Experimental procedures and data (S9-S20) IV, References (S21) V, MR Spectra for new compounds (S22-S141) 1
2 I. General information: All reactions were carried out under 2 atmosphere. All anhydrous solvents were purchased from Aldrich and stored over 4A molecular sieves. Reagents were purchased at commercial quality and were used without further purification. All MR spectra were run using CDCl 3 as solvent, unless otherwise specified. 1 H MR spectra were recorded at 500 MHz or 300 MHz, and chemical shifts are reported in ppm relative to TMS. 19 F MR spectra were recorded at 282 MHz, and chemical shifts are reported in ppm relative to CFCl 3 as the external standard. 13 C MR spectra were recorded at 125 MHz or 75 MHz with proton decoupling, and chemical shifts are reported in ppm relative to CDCl 3 (-77.0 ppm) as the reference. The visible light was generated from a fluorescent light bulb (daylight GE Energy Smart, 26 W, 1600 lumens). n-c 4 F 9 S 2 Cl, CF 3 CH 2 S 2 Cl, BrCF 2 CEt and CF 3 S 2 Cl were purchased from Synquest or Aldrich. HCF 2 S 2 Cl and FCH 2 S 2 Clwere prepared according to literature procedures. 2
3 II. Characterization of starting materials 1. Synthesis of substrates All starting materials were prepared according to previously reported procedures. 1 Characterization of non-previously reported compounds is given. -tert-butyl--(4-methoxybenzyl)methacrylamide (1a) Me 1 H MR (500 MHz, CDCl 3 ) δ 7.12 (d, J = 8.3 Hz, 2H), 6.86 (d, J = 8.4 Hz, 2H), 5.01 (s, 1H), 4.93 (s, 1H), 4.60 (s, 2H), 3.79 (d, J = 0.9 Hz, 3H), 1.92 (s, 3H), 1.41 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 16 H (M+H + ): , found: (4-(benzyloxy)benzyl)--tert-butylmethacrylamide (1b) 1 H MR (500 MHz, CDCl 3 ) δ 7.43 (d, J = 7.0 Hz, 2H), (m, 2H), 7.33 (t, J = 7.2 Hz, 1H), 7.13 (d, J = 8.7 Hz, 2H), 6.95 (d, J = 8.7 Hz, 2H), Bn 5.05 (s, 2H), 5.02 (s, 1H), (m, 1H), 4.61 (s, 2H), 1.93 (s, 3H), 1.42 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 22 H (M+H + ): , found: tert-butyl--(4-(4-methoxybenzyloxy)benzyl)methacrylamide (1c) 1 H MR (500 MHz, CDCl 3 ) δ 7.37 (d, J = 8.7 Hz, 2H), 7.14 (d, J = 8.7 Hz, 2H), 6.95 (t, J = 9.0 Hz, 4H), 5.04 (s, 1H), 4.99 (s, 2H), (m, 1H), PMB 4.63 (s, 2H), 3.84 (s, 3H), 1.95 (d, J = 1.3 Hz, 3H), 1.44 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (m), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s),
4 (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 23 H (M+H + ): , found: (4-(benzyloxy)benzyl)--butylmethacrylamide (1d) 1 H MR (500 MHz, CDCl 3 ) δ 7.43 (d, J = 7.1 Hz, 2H), 7.39 (t, J = 7.5 Hz, 2H), 7.33 (t, J = 7.2 Hz, 1H), 7.14 (d, J = 38.1 Hz, 2H), 6.94 (d, J = 7.8 Hz, Bn 2H), 5.14 (s, 1H), 5.05 (s, 3H), 4.55 (s, 2H), 3.26 (d, J = 38.6 Hz, 2H), 1.98 (s, 3H), (m, 2H), 1.24 (s, 2H), 0.89 (t, J = 7.2 Hz, 3H). 13 C MR (75 MHz, DMS) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 22 H (M+H + ): , found: (4-(benzyloxy)benzyl)--isopropylmethacrylamide (1e) 1 H MR (500 MHz, CDCl 3 ) δ 7.43 (d, J = 7.4 Hz, 2H), 7.38 (t, J = 7.5 Hz, 2H), 7.32 (t, J = 7.1 Hz, 1H), 7.18 (d, J = 6.6 Hz, 2H), 6.91 (d, J = 8.3 Hz, 2H), Bn 5.12 (s, 1H), 5.06 (s, 1H), 5.04 (s, 2H), 4.49 (s, 2H), 4.35 (s, 1H), 2.01 (s, 3H), 1.13 (d, J = 6.5 Hz, 6H). 13 C MR (75 MHz, DMS) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (m), (s). HRMS (ESI) calcd for C 21 H (M+H + ): , found: (4-(benzyloxy)benzyl)--cyclohexylmethacrylamide (1f) 1 H MR (300 MHz, DMS) δ 7.37 (ddd, J = 19.3, 14.1, 7.3 Hz, 5H), 7.15 (d, J = 8.5 Hz, 2H), 6.94 (d, J = 8.2 Hz, 2H), 5.11 (s, 1H), 5.04 (d, J = 13.6 Bn Hz, 2H), 4.99 (s, 1H), 4.45 (s, 2H), 3.76 (s, 1H), 1.90 (s, 3H), 1.65 (t, J = 14.7 Hz, 2H), 1.45 (dd, J = 28.0, 15.8 Hz, 5H), (m, 3H). 13 C MR (75 MHz, DMS) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 24 H (M+H + ): , found:
5 -(4-(benzyloxy)benzyl)--phenylmethacrylamide (1g) 1 H MR (500 MHz, CDCl 3 ) δ 7.42 (d, J = 7.0 Hz, 2H), 7.38 (t, J = 7.3 Hz, 2H), 7.32 (t, J = 7.1 Hz, 1H), 7.27 (d, J = 5.1 Hz, 1H), 7.22 (dd, J = 14.4, Bn 7.4 Hz, 2H), 7.14 (d, J = 8.4 Hz, 2H), (m, 2H), 6.87 (d, J = 8.5 Hz, 2H), 5.03 (s, 2H), 5.02 (s, 1H), 4.99 (d, J = 0.9 Hz, 1H), 4.90 (s, 2H), 1.77 (s, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 24 H (M+H + ): , found: benzyl--(4-(benzyloxy)benzyl)methacrylamide (1h) 1 H MR (500 MHz, CDCl 3 ) δ 7.45 (d, J = 7.3 Hz, 2H), 7.40 (t, J = 7.5 Hz, 2H), (m, 4H), 7.15 (d, J = 35.3 Hz, 4H), 6.96 (s, 2H), 5.19 (s, 1H), 5.15 (s, 1H), 5.07 (s, 2H), 4.48 (d, J = 26.7 Hz, 4H), 2.03 (s, 3H). 13 C MR (75 MHz, DMS) δ (s), (s), (s), (s), (s), Bn (s), (s), (s), (s), (s), (m), (s), (s), (s), (s). HRMS (ESI) calcd for C 25 H 26 2 (M+H + ): , found: (4-(benzyloxy)benzyl)--methylmethacrylamide (1i) 1 H MR (300 MHz, DMS) δ (m, 5H), 7.15 (s, 2H), (m, 2H), 5.18 (s, 1H), 5.08 (s, 2H), 5.00 (s, 1H), 4.47 (s, 2H), (m, Bn 3H), 1.88 (s, 3H). 13 C MR (75 MHz, DMS) δ (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 19 H 22 2 (M+H + ): , found: (4-(benzyloxy)-3-methoxybenzyl)--tert-butylmethacrylamide (1j) 1 H MR (500 MHz, CDCl 3 ) δ 7.43 (d, J = 7.4 Hz, 2H), 7.36 (t, J = 7.4 Hz, Me Bn 2H), 7.30 (t, J = 7.3 Hz, 1H), 6.85 (d, J = 8.2 Hz, 1H), 6.75 (d, J = 1.8 Hz, 1H), 6.69 (dd, J = 8.2, 2.0 Hz, 1H), 5.13 (s, 2H), 5.01 (s, 1H), (m, 5
6 1H), 4.60 (s, 2H), 3.86 (s, 3H), 1.93 (s, 3H), 1.43 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 23 H (M+H + ): , found: (4-(benzyloxy)-3-fluorobenzyl)--tert-butylmethacrylamide (1k) F 1 H MR (500 MHz, CDCl 3 ) δ 7.43 (d, J = 7.4 Hz, 2H), 7.38 (t, J = 7.4 Hz, 2H), 7.32 (t, J = 7.2 Hz, 1H), 6.96 (dd, J = 15.2, 7.0 Hz, 2H), 6.89 (d, J = 8.3 Bn Hz, 1H), 5.12 (s, 2H), 4.99 (s, 1H), 4.93 (s, 1H), 4.58 (s, 2H), 1.91 (s, 3H), 1.42 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (d, J = Hz), (d, J = 10.9 Hz), (s), (s), (d, J = 5.4 Hz), (s), (s), (s), (d, J = 3.5 Hz), (d, J = 1.9 Hz), (d, J = 19.2 Hz), (s), (s), (s), (s), (d, J = 13.8 Hz), (s). 19 F MR (282 MHz, CDCl 3 ) δ (dd, J = 11.7, 8.3 Hz). HRMS (ESI) calcd for C 22 H 27 F + 2 (M+H + ): , found: (4-(benzyloxy)-3-chlorobenzyl)--tert-butylmethacrylamide (1l) Cl 1 H MR (500 MHz, CDCl 3 ) δ 7.46 (d, J = 7.4 Hz, 1H), 7.39 (t, J = 7.4 Hz, 1H), 7.33 (t, J = 7.3 Hz, 1H), 7.23 (d, J = 2.2 Hz, 1H), 7.04 (dd, J = 8.4, 2.2 Bn Hz, 1H), 6.94 (d, J = 8.5 Hz, 1H), 5.14 (s, 1H), 4.99 (s, 1H), (m, 1H), 4.58 (s, 1H), 1.92 (d, J = 1.1 Hz, 2H), 1.42 (s, 5H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd C 22 H 27 Cl + 2, For (M+H + ): , found: (4-(benzyloxy)-3-bromobenzyl)--tert-butylmethacrylamide (1m) 1 H MR (500 MHz, CDCl 3 ) δ 7.47 (d, J = 7.5 Hz, 2H), (m, 3H), Br Bn 7.33 (t, J = 7.3 Hz, 1H), 7.09 (dd, J = 8.4, 2.2 Hz, 1H), 6.91 (d, J = 8.5 Hz, 1H), 5.14 (s, 2H), (m, 1H), (m, 1H), 4.58 (s, 2H), (m, 3H), 1.42 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), 6
7 (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 22 H 27 Br + 2 (M+H + ): , found: (4-(benzyloxy)-3,5-dimethoxybenzyl)--tert-butylmethacrylamide (1o) Me 1 H MR (500 MHz, CDCl 3 ) δ 7.46 (d, J = 7.0 Hz, 2H), (m, 2H), (m, 1H), 6.41 (s, 2H), 5.00 (d, J = 2.6 Hz, 3H), 4.95 (dd, J = 13.3, Bn 12.0 Hz, 1H), 4.61 (s, 2H), 3.79 (s, 6H), 1.93 (s, 3H), 1.45 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), Me (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 24 H (M+H + ): , found: (4-(benzyloxy)-3,5-dimethylbenzyl)--tert-butylmethacrylamide (1n) tbu Bn 1 H MR (500 MHz, CDCl 3 ) δ 7.47 (d, J = 6.9 Hz, 2H), 7.40 (t, J = 7.3 Hz, 2H), 7.35 (t, J = 7.2 Hz, 1H), 6.86 (s, 2H), 5.02 (s, 1H), 4.94 (s, 1H), 4.81 (s, 2H), 4.58 (s, 2H), 2.28 (s, 6H), 1.94 (s, 3H), 1.44 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (m), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 24 H (M+H + ): , found: ((4-(benzyloxy)naphthalen-1-yl)methyl)--tert-butylmethacrylamide (1p) tbu 1 H MR (500 MHz, CDCl 3 ) δ 8.45 (d, J = 8.2 Hz, 1H), 7.86 (d, J = 8.4 Hz, Bn 1H), (m, 4H), 7.45 (t, J = 7.4 Hz, 3H), 7.37 (dd, J = 18.3, 11.0 Hz, 1H), 6.94 (d, J = 7.9 Hz, 1H), 5.26 (s, 2H), 5.03 (s, 2H), 4.99 (s, 1H), 4.80 (s, 1H), 1.95 (s, 3H), 1.54 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), 7
8 (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 26 H (M+H + ): , found: (4-(benzyloxy)benzyl)--tert-butylacrylamide (1q) 1 H MR (500 MHz, CDCl 3 ) δ 7.44 (d, J = 7.1 Hz, 2H), 7.39 (t, J = 7.5 Hz, 2H), 7.33 (t, J = 7.2 Hz, 1H), 7.15 (d, J = 8.5 Hz, 2H), 6.97 (d, J = 8.6 Hz, Bn 2H), 6.39 (dd, J = 16.6, 10.1 Hz, 1H), 6.30 (dd, J = 16.7, 2.3 Hz, 1H), 5.54 (dd, J = 10.1, 2.3 Hz, 1H), 5.06 (s, 2H), 4.57 (s, 2H), 1.45 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). HRMS (ESI) calcd for C 21 H (M+H + ): , found: Synthesis of mono and difluoromethyl sulfonyl chloride The Difluoromethyl sulfonyl chloride was prepared according to literature procedures, and its 1 H MR and 19 F MR were consistent with those reported in the literature. 2 Cl SH i) ah ii) H 2CFCl SCH 2 F Cl 2 DMF, 70 C Cl H2/DCM, -10 C H 2 CFS 2 Cl SH 1.5 eq HCF 2 Cl 2.5 eq ah Hexanes/60 C 2 h S CF 2 H Cl 2, H 2-10 C HCF 2 S 2 Cl III. Experimental procedures and data fac-ir(ppy) 3 catalyzed difluoromethylation of -benzylacrylamides coupled with dearomatization To an oven-dried mm (8 ml) borosilicate vial equipped with a magnetic stirrer, were added -benzylacrylamide (64.6 mg, 0.2 mmol), fac-ir(ppy) 3 (2.4 mg, mmol, eq) and K 2 HP 4 (68 mg, 0.4 mmol, 2.0 equiv). To this mixture were added 2 ml CH 3 C, 8 mg deionized 8
9 water and CF 2 HS 2 Cl (60 mg, 0.4 mmol, 2 equiv) under a blanket of nitrogen. The vial was sealed, and stirred under visible light at room temperature for 18 hr. After this time, the CH 3 C was removed in vacuo, and the residue purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (2:1). This gave product 2a as light yellow oil (48.7 mg, 82% yield). CF 2 H 2-tert-butyl-4-(2,2-difluoroethyl)-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8- dione (2a) 1 H MR (500 MHz, CDCl 3 ) δ 6.86 (ddd, J = 8.4, 5.9, 3.0 Hz, 2H), 6.37 (ddd, J = 12.2, 10.0, 4.7 Hz, 2H), 6.08 (tdd, J = 56.4, 5.6, 3.6 Hz, 1H), 3.51 (d, J = 10.5 Hz, 1H), 3.27 (d, J = 10.5 Hz, 1H), (m, 1H), 1.68 (qd, J = 15.1, 5.7 Hz, 1H), 1.37 (s, 9H), 1.20 (s, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (dd, J = 239.7, Hz), (s), (dd, J = 6.7, 3.0 Hz), (s), (s), (t, J = 22.4 Hz), (s), (d, J = 1.8 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (AB, ddddd, J = 284.8, 38.7, 22.6, 15.5, 1.5 Hz, 1F), (AB, ddt, J = 287.6, 55.8, 14.6 Hz, 1F). HRMS (ESI) calcd for C 16 H 22 F (M+H + ): , found: butyl-4-(2,2-difluoroethyl)-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (2d) Prepared according to general method and isolated in 83% yield after chromoatography as light yellow oil (49.5 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.87 (ddd, J = 17.0, 10.2, 3.0 Hz, 2H), 6.41 (ddd, J = 23.0, 10.0, 1.4 Hz, 2H), CF 2 H 6.14 (tdd, J = 56.2, 5.7, 3.4 Hz, 1H), 3.53 (d, J = 10.5 Hz, 1H), (m, 2H), 3.19 (d, J = 10.5 Hz, 1H), (m, 1H), 1.75 (ddd, J = 30.0, 15.2, 5.8 Hz, 1H), (m, 2H), 1.32 (dq, J = 14.6, 7.3 Hz, 2H), 1.26 (s, 3H), 0.93 (t, J = 7.3 Hz, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (dd, J = 240.0, Hz), (s), (dd, J = 7.0, 2.8 Hz), (s), (s), (m), (s), (s), (d, J = 2.2 Hz), (s). 19 F MR (282 MHz, CDCl 3 ) δ (AB, ddddd, J = 288.2, 23.8, 17.3, 16.0, 1.9 Hz, 1F), (AB, ddt, J = 288.2, 55.8, 14.3 Hz, 1F). HRMS (ESI) calcd for C 16 H 22 F (M+H + ): , found:
10 diene-3,8-dione (2f) Prepared according to general method and isolated in 80% yield after CF 2 H chromoatography as yellow oil (51.7 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.87 (dd, J = 10.2, 3.1 Hz, 1H), 6.83 (dd, J = 10.2, 3.1 Hz, 1H), 6.42 (dd, J = 10.2, 1.9 Hz, 1H), 6.37 (dd, J = 10.2, 1.9 Hz, 1H), 6.13 (tdd, J = 55.9, 5.7, 3.4 Hz, 1H), 3.95 (tt, J = 11.6, 3.7 Hz, 1H), 3.44 (d, J = 10.5 Hz, 1H), 3.19 (d, J = 10.5 Hz, 1H), (m, 1H), (m, 6H), (m, 4H), 1.24 (d, J = 1.5 Hz, 3H), (m, 1H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (dd, J = 239.9, Hz), (s), (dd, J = 6.9, 3.0 Hz), (s), (s), (m), (s), (s), (s), (s), (s), (d, J = 2.1 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (AB, ddddd, J = 287.9, 56.5, 23.4, 15.7, 1.8 Hz, 1F), (AB, ddt, J = 287.9, 55.9, 14.6 Hz, 1F). HRMS (ESI) calcd for C 18 H 24 F (M+H + ): , found: (2,2-difluoroethyl)-2-isopropyl-4-methyl-2-azaspiro[4.5]deca-6,9- diene-3,8-dione (2e) Prepared according to general method and isolated in 82% yield after chromoatography as light yellow oil (46.5 mg): 1 H MR (500 MHz, CDCl 3 ) δ CF 2 H 6.88 (dd, J = 10.2, 3.0 Hz, 1H), 6.83 (dd, J = 10.2, 3.1 Hz, 1H), 6.43 (dd, J = 10.3, 1.8 Hz, 1H), 6.39 (dd, J = 10.2, 1.8 Hz, 1H), 6.14 (tdd, J = 56.3, 5.7, 3.4 Hz, 1H), 4.38 (hept, J = 6.8 Hz, 1H), 3.43 (d, J = 10.5 Hz, 1H), 3.17 (d, J = 10.5 Hz, 1H), (m, 1H), 1.74 (qd, J = 15.1, 5.8 Hz, 1H), 1.25 (d, J = 1.4 Hz, 3H), 1.14 (t, J = 7.0 Hz, 6H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (dd, J = 239.9, Hz), (dd, J = 6.8, 3.0 Hz), (s), (s), (s), (m), (s), (s), (d, J = 2.1 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (AB, ddddd, J = 287.9, 56.6, 23.4, 15.7, 1.7 Hz, 1F), (AB, ddt, J = 287.9, 55.8, 14.6 Hz, 1F). HRMS (ESI) calcd for C 15 H 20 F (M+H + ): , found: cyclohexyl-4-(2,2-difluoroethyl)-4-methyl-2-azaspiro[4.5]deca-6,9-4-(2,2-difluoroethyl)-4-methyl-2-phenyl-2-azaspiro[4.5]deca-6,9-diene- 3,8-dione (2g) CF 2 H Prepared according to general method and isolated in 48% yield after chromoatography as yellow oil (30.4 mg): 1 H MR (500 MHz, CDCl 3 ) δ 7.57 (dd, J = 8.7, 1.1 Hz, 2H), (m, 2H), (m, 1H), 7.00 (dd, J 10
11 = 10.5, 2.0 Hz, 2H), (m, 2H), 6.20 (tdd, J = 55.7, 5.8, 3.4 Hz, 1H), 4.03 (d, J = 10.4 Hz, 1H), 3.69 (d, J = 10.4 Hz, 1H), (m, 1H), 1.89 (ddd, J = 30.1, 15.1, 5.8 Hz, 1H), 1.41 (d, J = 1.7 Hz, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (dd, J = 240.2, Hz), (s), (dd, J = 7.0, 2.9 Hz), (s), (dd, J = 23.2, 22.3 Hz), (d, J = 2.3 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (AB, ddddd, J = 287.9, 56.5, 23.5, 15.6, 1.9 Hz, 1F), (AB, ddt, J = 287.9, 55.6, 14.3 Hz, 1F).HRMS (ESI) calcd for C 18 H 18 F (M+H + ): , found: (4-(benzyloxy)benzyl)-3-(2,2-difluoroethyl)-3-methylindolin-2-one (2g ) Bn Prepared according to general method and isolated in 50% yield after chromoatography as yellow oil (41.0 mg): 1 H MR (500 MHz, CDCl 3 ) δ 7.37 (ddd, J = 27.9, 14.0, 7.0 Hz, 5H), (m, 4H), 7.06 (t, J = 7.5 Hz, 1H), 6.93 (d, J = 8.6 Hz, 2H), 6.79 (d, J = 7.8 Hz, 1H), 5.61 (tdd, J = CF 2 H 56.1, 6.4, 3.3 Hz, 1H), 5.03 (s, 2H), 4.93 (d, J = 15.4 Hz, 1H), 4.81 (d, J = 15.4 Hz, 1H), 2.59 (qd, J = 14.2, 6.6 Hz, 1H), (m, 1H), 1.46 (s, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (t, J = Hz), (s), (s), (s), (t, J = 5.3 Hz), (s), (t, J = 21.9 Hz), (s). 19 F MR (282 MHz, CDCl 3 ) δ (ddd, J = 56.0, 14.5, 4.2 Hz δ (dd, J = 56.1, 14.8 Hz). HRMS (ESI) calcd for C 25 H 24 F 2 2 (M+H + ): , found: benzyl-4-(2,2-difluoroethyl)-4-methyl-2-azaspiro[4.5]deca-6,9-diene- 3,8-dione (2h) Bn CF 2 H Prepared according to general method and isolated in 82% yield after chromoatography as yellow oil (54.4 mg): 1 H MR (500 MHz, CDCl 3 ) δ (m, 3H), 7.23 (d, J = 6.8 Hz, 2H), 6.79 (ddd, J = 16.9, 10.2, 3.1 Hz, 2H), 6.39 (dd, J = 10.2, 1.8 Hz, 1H), 6.33 (dd, J = 10.1, 1.8 Hz, 1H), 6.19 (tdd, J = 56.1, 5.8, 3.4 Hz, 1H), 4.55 (d, J = 14.5 Hz, 1H), 4.45 (d, J = 14.4 Hz, 1H), 3.36 (d, J = 10.6 Hz, 1H), 3.06 (d, J = 10.6 Hz, 1H), (m, 1H), 1.79 (qd, J = 15.2, 5.8 Hz, 1H), 1.28 (d, J = 1.5 Hz, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (dd, J = 240.1, Hz), (s), (dd, J = 7.0, 2.8 Hz), (s), (s), (m), (d, J = 2.1 Hz). 19 F MR (282 MHz, 11
12 CDCl 3 ) δ (AB, ddddd, J = , 56.4, 23.5, 15.6, 1.6 Hz, 1F), (AB, ddt, J = , 55.8, 14.4 Hz, 1F). HRMS (ESI) calcd for C 19 H 20 F (M+H + ): , found: tert-butyl-4-(2,2-difluoroethyl)-7-methoxy-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (2j) Prepared according to general method and isolated in 76% yield after chromoatography as yellow oil (50.0 mg): 1 H MR (500 MHz, CDCl 3 ) δ Me 6.90 (ddd, J = 12.9, 10.1, 2.7 Hz, 1H (both isomers)), 6.44 (dd, J = 12.0, 10.2 CF 2 H Hz, 1H (both isomers)), (m, 1H (isomers A)), δ 6.09 (tdd, J = 56.0, 5.5, 3.5 Hz, 1H (isomers B)), 5.69 (dd, J = 14.1, 2.6 Hz, 1H (isomers A)), 5.68 (d, J = 2.6 Hz, 1H (isomers B)), 3.70 (s, 1H (isomers A)), 3.68 (s, 3H (isomers B)), 3.56 (d, J = 10.5 Hz, 1H (isomers A)), 3.54 (d, J = 10.5 Hz, 1H (isomers B)), 3.36 (d, J = 10.4 Hz, 1H (isomers A)), 3.28 (d, J = 10.4 Hz, 1H (isomers B)), (m, 1H (both isomers)), (m, 1H (both isomers)), 1.42 (s, 9H (isomers A)), 1.41 (s, 9H (isomers B)), 1.27 (d, J = 1.7 Hz, 3H (isomers A)), 1.19 (s, 3H (isomers B)). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (dd, J = 239.9, Hz), δ (dd, J = 239.8, Hz), (s), (s), (s), (s), (s), (s), (dd, J = 6.2, 3.4 Hz), (dd, J = 6.5, 3.1 Hz), (s), (s), (t, J = 22.4 Hz), (t, J = 22.3 Hz), (d, J = 1.6 Hz), (s), (s) F MR (282 MHz, CDCl 3 ) δ (m). HRMS (ESI) calcd for C 17 H 24 F 2 3 (M+H + ): , found: F 2-tert-butyl-4-(2,2-difluoroethyl)-7-fluoro-4-methyl-2- azaspiro[4.5]deca-6,9-diene-3,8-dione (2k) Prepared according to general method and isolated in 77% yield after CF 2 H chromoatography as pale yellow oil (48.6 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.91 (td, J = 9.7, 2.7 Hz, 1H (both isomers)), (m, 2H (both isomers)), 6.14 (tdd, J = 56.4, 6.1, 2.8 Hz, 1H (isomers A)), 6.10 (tdd, J = 56.2, 5.7, 3.2 Hz, 1H (isomers B)), 3.58 (d, J = 10.6 Hz, 1H (isomers A)), 3.56 (dd, J = 10.5, 1.2 Hz, 1H (isomers B)), 3.38 (d, J = 10.6 Hz, 1H (isomers A)), 3.32 (d, J = 10.6 Hz, 1H (isomers B)), (m, 1H (both isomers)), (m, 1H (both isomers) ), 1.40 (s, 9H (both isomers)), 1.24 (s, 3H (isomers A)), 1.21 (s, 3H (isomers B)). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (d, J = 48.5 Hz), (d, J = 48.4 Hz), (d, J = 2.1 Hz), (d, J = 2.1 Hz), (d, J = 4.5 Hz), (d, J = 4.6 Hz), (d, J = 13.9 Hz), (d, J = 14.7 Hz), (m), (s), (s), (m), (s), (t, J = 2.9 Hz), (d, J = 5.2 Hz), (d, J = 5.5 Hz), (m),
13 37.86 (m), (s), (d, J = 2.3 Hz), (d, J = 2.1 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (m, 2F), (dd, J = 13.1, 6.9 Hz, 1F (isomers A)), (dd, J = 13.0, 6.9 Hz 1F, (isomers B)). HRMS (ESI) calcd for C 16 H 21 F (M+H + ): , found: tert-butyl-7-chloro-4-(2,2-difluoroethyl)-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (2l) Prepared according to general method and isolated in 84% yield after chromoatography as yellow oil (55.7 mg): 1 H MR (500 MHz, CDCl 3 ) δ 7.03 Cl (d, J = 1.6 Hz, 1H (both isomers)), 6.90 (td, J = 9.7, 2.7 Hz, 1H (both isomers)), CF 2 H 6.49 (dd, J = 14.0, 10.2 Hz, 1H (both isomers)), (m, 1H (both isomers)), 3.58 (d, J = 10.6 Hz, 1H (isomers A)), δ 3.55 (d, J = 10.7 Hz, 1H (isomers B)), 3.37 (d, J = 10.6 Hz, 1H (isomers A)), 3.33 (d, J = 10.6 Hz, 1H (isomers B)), (m, 1H (both isomers)), (m, 1H (both isomers)), 1.40 (s, 9H (isomers A)), 1.40 (s, 9H (isomers B)), 1.25 (s, 3H (isomers A)), 1.22 (s, 3H (isomers B)). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (dd, J = 239.9, Hz), δ (dd, J = 240.0, Hz), (s), (s), (dd, J = 7.0, 2.3 Hz), (dd, J = 7.3, 2.2 Hz), (s), (s), (s), (s), (dd, J = 22.1, 14.2 Hz), (dd, J = 23.1, 14.2 Hz), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (m). HRMS (ESI) calcd for C 16 H 21 ClF (M+H + ): , found: bromo-2-tert-butyl-4-(2,2-difluoroethyl)-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (2m) Prepared according to general method and isolated in 61% yield after chromoatography as yellow oil (45.9 mg): 1 H MR (500 MHz, CDCl 3 ) δ 7.31 Br (d, J = 2.8 Hz, 1H), 6.91 (dd, J = 10.1, 2.8 Hz, 1H), 6.54 (d, J = 10.1 Hz, 1H), CF 2 H 6.15 (tdd, J = 55.7, 5.9, 3.0 Hz, 1H), 3.55 (d, J = 10.7 Hz, 1H), 3.39 (d, J = 10.6 Hz, 1H), (m, 1H), (m, 1H), 1.43 (s, 9H), 1.25 (d, J = 1.7 Hz, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (dd, J = 240.1, Hz), (s), (s), (dd, J = 7.1, 2.4 Hz), (s), (dd, J = 23.1, 22.2 Hz), (s), (d, J = 2.4 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (m). HRMS (ESI) calcd for C 16 H 21 BrF (M+H + ): , found: tert-butyl-4-(2,2-difluoroethyl)-4,7,9-trimethyl-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (2n) 13
14 Prepared according to general method and isolated in 93% yield after chromoatography as white solide (60.7 mg): 1 H MR (500 MHz, CDCl 3 ) δ CF 2 H 6.61 (s, 2H), 6.10 (t, J = 56.4 Hz, 1H), 3.49 (d, J = 10.2 Hz, 1H), 3.24 (d, J = 10.3 Hz, 1H), (m, 1H), 1.93 (s, 6H), 1.67 (d, J = 14.8 Hz, 1H), 1.40 (s, 9H), 1.19 (s, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (dd, J = 239.7, Hz), (s), (s), (dd, J = 6.6, 2.8 Hz), (s), (t, J = 22.3 Hz), (s), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (AB, ddddd, J = , 56.7, 22.8, 15.9, 1.9 Hz Hz, 1F), (AB, ddt, J = , 56.1, 15.0 Hz, 1F). HRMS (ESI) calcd for C 18 H 26 F (M+H + ): , found: tert-butyl-4-(2,2-difluoroethyl)-7,9-dimethoxy-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8- dione (2o) Prepared according to general method and isolated in 53% yield after Me chromoatography as yellow oil (37.9 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.10 (ddd, J = 56.1, 7.9, 3.9 Hz, 1H), 5.76 (s, 1H), 5.72 (s, 1H), 3.67 (s, 3H), CF 2 H 3.65 (s, 3H), 3.55 (d, J = 10.3 Hz, 1H), 3.31 (d, J = 10.3 Hz, 1H), 2.09 (ddd, Me J = 19.8, 17.3, 8.5 Hz, 1H), 1.67 (qd, J = 15.1, 5.6 Hz, 1H), 1.40 (d, J = 0.5 Hz, 10H), 1.20 (s, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (dd, J = 239.6, Hz), (s), (s), (s), (s), (s), (s), (dd, J = 6.6, 2.9 Hz), (s), (t, J = 22.3 Hz), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (AB, dddd, J = , 38.9, 23.0, 16.6 Hz, 1F), (AB, ddt, J = , 56.0, 14.8 Hz, 1F). HRMS (ESI) calcd for C 18 H 26 F (M+H + ): , found: '-tert-butyl-4'-(2,2-difluoroethyl)-4'-methyl-4H-spiro[naphthalene-1,3'-pyrrolidine]-4,5'-dione (2p) Prepared according to general method and isolated in 78% yield after chromoatography as yellow oil (54.3 mg): 1 H MR (500 MHz, CDCl 3 ) δ 8.22 CF 2 H (d, J = 7.8 Hz, 1H), 7.64 (d, J = 8.1 Hz, 1H), 7.57 (t, J = 7.7 Hz, 1H), 7.49 (t, J = 7.5 Hz, 1H), 7.02 (d, J = 10.4 Hz, 1H), 6.62 (d, J = 10.4 Hz, 1H), 6.00 (tdd, J = 56.3, 5.9, 2.8 Hz, 1H), 3.85 (d, J = 10.6 Hz, 1H), 3.72 (d, J = 10.6 Hz, 1H), (m, 1H), (m, 9H), 1.42 (dd, J = 15.6, 9.5 Hz, 1H), 1.37 (d, J = 8.6 Hz, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (dd, J = 239.7, Hz), (s), (s), (dd, J = 7.5, 2.2 Hz), (s), 14
15 37.84 (dd, J = 23.1, 21.7 Hz), (s), (d, J = 2.4 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (m). HRMS (ESI) calcd for C 20 H 24 F (M+H + ): , found: tert-butyl-4-(2,2-difluoroethyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (2q) Prepared according to general method and isolated in 82% yield after chromoatography as yellow oil (46.5 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.84 CF 2 H (dd, J = 10.2, 2.9 Hz, 1H), 6.80 (dd, J = 10.1, 2.9 Hz, 1H), 6.40 (s, 1H), 6.38 (s, 1H), 6.10 (tdd, J = 57.1, 6.3, 3.3 Hz, 1H), 3.58 (d, J = 10.2 Hz, 1H), 3.29 (d, J = 10.2 Hz, 1H), 2.83 (dd, J = 7.8, 5.8 Hz, 1H), (m, 1H), (m, 1H), 1.40 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (t, J = Hz), (s), (s), (dd, J = 7.1, 3.6 Hz), (s), (dd, J = 23.4, 22.1 Hz), (s). 19 F MR (282 MHz, CDCl 3 ) δ (AB, dddd, J = 283.1, 56.7, 14.7, 11.1 Hz, 1F), (AB, ddt, J = 283.1, 57.5, 26.4, 14.3 Hz, 1F). HRMS (ESI) calcd for C 15 H 20 F (M+H + ): , found: ethyl 3-(2-tert-butyl-4-methyl-3,8-dioxo-2-azaspiro[4.5]deca-6,9-dien-4-yl)-2,2-difluoropropanoate (3b) Prepared according to general method and isolated in 72% yield after chromoatography as yellow oil (53.2 mg): 1 H MR (500 MHz, CDCl 3 ) δ (m, 2H), 6.43 (dd, J = 8.4, 3.8 Hz, 1H), (m, 1H), CF 2 C 2 Et 4.26 (q, J = 7.1 Hz, 2H), 3.55 (d, J = 10.4 Hz, 1H), 3.20 (d, J = 10.4 Hz, 1H), 2.63 (ddd, J = 24.6, 17.3, 16.1 Hz, 1H), 2.06 (ddd, J = 24.7, 15.9, 8.8 Hz, 1H), 1.40 (s, 9H), 1.35 (d, J = 2.2 Hz, 3H), 1.31 (t, J = 7.1 Hz, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (t, J = 32.5 Hz), (s), (d, J = 1.0 Hz), (d, J = 1.9 Hz), (s), (dd, J = 255.3, Hz), (s), (s), (s), (s), (s), (dd, J = 24.3, 21.7 Hz), (s), (d, J = 4.8 Hz), (s). 19 F MR (282 MHz, CDCl 3 ) δ (AB, ddd, J = 264.2, 24.3, 9.0 Hz, 1F), (AB, ddd, J = 264.2, 23.9, 18.3 Hz, 1F). HRMS (ESI) calcd for C 19 H 26 F (M+H + ): , found: tert-butyl-4-methyl-4-(2,2,2-trifluoroethyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (4b) 15
16 Prepared according to general method and isolated in 88% yield after chromoatography as yellow oil (55.6 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.89 CF 3 (dd, J = 10.2, 3.1 Hz, 1H), 6.85 (dd, J = 10.2, 3.1 Hz, 1H), 6.41 (dd, J = 10.3, 1.5 Hz, 1H), (m, 1H), 3.57 (d, J = 10.5 Hz, 1H), 3.18 (d, J = 10.5 Hz, 1H), 2.65 (dq, J = 15.9, 12.3 Hz, 1H), 2.14 (dq, J = 15.8, 11.3 Hz, 1H), 1.40 (s, 9H), 1.33 (s, 3H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (q, J = Hz), (s), (s), (s), (s), (q, J = 29.3 Hz), (s), (d, J = 1.6 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 11.8 Hz). HRMS (ESI) calcd for C 16 H 21 F (M+H + ): , found: CF 2 CF 2 CF 2 CF 3 Prepared according to general method and isolated in 85% yield after chromoatography as yellow oil (79.2 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.92 (d, J = 10.3 Hz, 1H), 6.86 (d, J = 10.3 Hz, 1H), 6.43 (d, J = 10.4 Hz, 1H), 6.36 (d, J = 10.4 Hz, 1H), 3.60 (d, J = 10.4 Hz, 1H), 3.18 (d, J = 10.5 Hz, 1H), (m, 1H), 2.16 (dd, J = 36.8, 16.4 Hz, 1H), 1.41 (s, 12H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (d, J = 2.5 Hz), (d, J = 3.8 Hz), (s), (m), (s), (s), (s), (s), (t, J = 21.0 Hz), (s), (d, J = 5.2 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (ddd, J = 12.6, 6.3, 3.0 Hz, 3F), (d, J = Hz, 1F), (m, 1F), (m, 2F), (ddd, J = 27.1, 16.2, 8.0 Hz, 2F). HRMS (ESI) calcd for C 19 H 21 F (M+H + ): , found: S 2 CH 2 F 2-tert-butyl-4-methyl-4-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-2- azaspiro[4.5]deca-6,9-diene-3,8-dione (5b) 2-tert-butyl-4-((fluoromethylsulfonyl)methyl)-4-methyl-2- azaspiro[4.5]deca-6,9-diene-3,8-dione (6a) Prepared according to general method and isolated in 78% yield after chromoatography as yellow oil (53.6 mg): 1 H MR (500 MHz, CDCl 3 ) δ (m, 2H), 6.45 (dd, J = 10.4, 1.6 Hz, 1H), 6.40 (dd, J = 10.4, 1.6 Hz, 1H), 5.17 (dd, J = 47.0, 10.3 Hz, 1H), 5.00 (dd, J = 46.8, 10.3 Hz, 1H), 3.59 (d, J = 10.6 Hz, 1H), 3.49 (d, J = 15.0 Hz, 1H), 3.27 (d, J = 10.6 Hz, 1H), 3.00 (d, J = 15.0 Hz, 1H), 1.52 (s, 3H), 1.39 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (d, J = Hz), (s), (s), (s), (s), (s), (s), (s). 19 F MR (282 MHz, 16
17 CDCl 3 ) δ (t, J = 46.9 Hz). HRMS (ESI) calcd for C 16 H 23 F 4 S + (M+H + ): , found: Prepared according to general method and isolated in 81% yield after S 2 CH 2 CF 3 chromoatography as yellow oil (63.8 mg): 1 H MR (500 MHz, CDCl 3 ) δ (m, 2H), 6.44 (dd, J = 8.6, 3.3 Hz, 1H), 6.39 (dd, J = 8.5, 3.2 Hz, 1H), (m, 1H), 3.88 (dq, J = 15.6, 9.3 Hz, 1H), 3.58 (dd, J = 16.4, 12.8 Hz, 2H), 3.26 (d, J = 10.6 Hz, 1H), 3.05 (d, J = 15.0 Hz, 1H), 1.53 (s, 3H), 1.39 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (q, J = Hz), (d, J = 2.1 Hz), (q, J = 31.4 Hz), (s), (s), (s), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 9.3 Hz). HRMS (ESI) calcd for C 17 H 23 F 3 4 S + (M+H + ): , found: tert-butyl-4-methyl-4-((2,2,2-trifluoroethylsulfonyl)methyl)-2-azaspiro[4.5]deca-6,9-diene-3,8- dione (7a) 2-cyclohexyl-4-((fluoromethylsulfonyl)methyl)-4-methyl-2- azaspiro[4.5]deca-6,9-diene-3,8-dione (6f) Prepared according to general method and isolated in 52% yield after chromoatography as yellow oil (38.4 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.88 (ddd, J = 19.7, 10.3, 2.9 Hz, 2H), 6.43 (ddd, J = 31.6, 10.1, 0.8 Hz, S 2 CH 2 F 2H), 5.22 (dt, J = 19.6, 9.8 Hz, 1H), (m, 1H), 3.95 (td, J = 11.5, 3.6 Hz, 1H), 3.51 (dd, J = 12.8, 6.1 Hz, 2H), 3.21 (d, J = 10.6 Hz, 1H), (m, 1H), (m, 6H), 1.54 (s, 3H), (m, 4H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (d, J = Hz), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 46.9 Hz). HRMS (ESI) calcd for C 18 H 25 F 4 S + (M+H + ): , found: cyclohexyl-4-methyl-4-((2,2,2-trifluoroethylsulfonyl)methyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (7f) Prepared according to general method and isolated in 51% yield after chromoatography as yellow oil (42.8 mg): 1 H MR (500 MHz, CDCl 3 ) δ 6.87 (dd, J = 23.4, 10.4 Hz, 2H), 6.46 (dd, J = 33.6, 10.4 Hz, 2H), S 2 CH 2 CF 3 17
18 4.26 (dq, J = 17.8, 8.9 Hz, 1H), (m, 2H), 3.59 (d, J = 15.2 Hz, 1H), 3.53 (d, J = 10.7 Hz, 1H), 3.22 (d, J = 10.4 Hz, 1H), 3.04 (d, J = 15.2 Hz, 1H), 1.83 (s, 2H), (m, 3H), 1.57 (s, 3H), (m, 4H), 1.08 (d, J = 12.7 Hz, 1H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (q, J = Hz), (s), (dd, J = 62.8, 31.2 Hz), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 9.2 Hz). HRMS (ESI) calcd for C 19 H 25 F 3 4 S + (M+H + ): , found: tert-butyl-4-((fluoromethylsulfonyl)methyl)-7-methoxy-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8- dione (6j) Prepared according to general method and isolated in 80% yield after chromoatography as yellow oil (59.8 mg): 1 H MR (500 MHz, CDCl 3 ) Me δ 6.89 (dd, J = 2.7, 1.6 Hz, 1H (isomer A)), 6.87 (dd, J = 2.7, 1.6 Hz, S 2 CH 2 F 1H (isomer B)), 6.46 (d, J = 10.2 Hz, 1H (isomer A)), 6.42 (d, J = 10.1 Hz, 1H (isomer B)), 5.75 (dd, J = 63.6, 2.7 Hz, 2H (both isomer)), (m, 4H (both isomer)), 3.71 (s, 3H (isomer A)), 3.67 (s, 3H (isomer B)), 3.61 (d, J = 10.5 Hz, 2H (both isomer)), 3.45 (t, J = 15.7 Hz, 2H (both isomer)), 3.35 (d, J = 10.4 Hz, 1H (isomer A)), 3.26 (d, J = 10.5 Hz, 1H (isomer B)), 3.13 (d, J = 15.0 Hz, 1H (isomer A)), 2.91 (d, J = 15.0 Hz, 1H (isomer B)), 1.57 (s, 3H (isomer A)), 1.47 (s, 3H (isomer B)), 1.41 (s, 9H (isomer A)), 1.40 (s, 9H (isomer B)). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (d, J = Hz), (d, J = Hz), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 46.8 Hz (isomer A)), (t, J = 46.9 Hz (isomer B)). HRMS (ESI) calcd for C 17 H 25 F 5 S + (M+H + ): , found: tert-butyl-7-methoxy-4-methyl-4-((2,2,2-trifluoroethylsulfonyl)methyl)-2-azaspiro[4.5]deca-6,9-diene- 3,8-dione (7j) Prepared according to general method and isolated in 85% yield after chromoatography as yellow oil (72.0 mg): 1 H MR (500 MHz, Me CDCl 3 ) δ 6.88 (t, J = 3.2 Hz, 1H (isomers A)), 6.86 (t, J = 3.2 Hz, S 2 CH 2 CF 3 1H (isomers B)), 6.44 (d, J = 10.2 Hz, 1H (isomers A)), 6.40 (d, J = 10.1 Hz, 1H (isomers B)), 5.79 (d, J = 2.6 Hz, 1H (isomers A)), 5.67 (d, J = 2.6 Hz, 1H (isomers B)), (m, 2H (isomers A)), 3.91 (ddd, J = 18.4, 15.7, 9.3 Hz, 2H (isomers B)), 3.69 (s, 3H (isomers A)), 3.65 (s, 3H (isomers B)), 3.63 (d, J = 4.9 Hz, 1H (isomers A)),
19 (d, J = 5.0 Hz, 1H (isomers B)), 3.53 (d, J = 15.1 Hz, 1H (both isomers)), 3.34 (d, J = 10.5 Hz, 1H (isomers A)), 3.25 (d, J = 10.6 Hz, 1H (isomers B)), 3.16 (d, J = 15.1 Hz, 1H (isomers A)), 2.97 (d, J = 15.0 Hz, 1H (isomers B)), 1.57 (s, 3H (isomers A)), 1.48 (s, 3H (isomers B)), 1.40 (s, 9H (isomers A)), 1.39 (s, 9H (isomers B)). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (q, J = Hz), δ (q, J = Hz), (s), (d, J = 2.4 Hz), (s), (q, J = 31.3 Hz), δ (q, J = 31.4 Hz), (d, J = 6.0 Hz), (d, J = 3.8 Hz), (s), (s), (s), (s), (s), (d, J = 2.6 Hz), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 9.2 Hz), (m). HRMS (ESI) calcd for C 18 H 25 F 3 5 S + (M+H + ): , found: tert-butyl-7-fluoro-4-((fluoromethylsulfonyl)methyl)-4-methyl-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (6k) Prepared according to general method and isolated in 70% yield after chromoatography as yellow oil (50.7 mg): 1 H MR (500 MHz, CDCl 3 ) δ F 6.93 (ddd, J = 9.9, 5.8, 2.7 Hz, 1H (both isomer)), 6.50 (dd, J = 10.2, 7.0 S 2 CH 2 F Hz, 1H (isomer A)), 6.45 (dd, J = 9.7, 2.9 Hz, 1H (both isomer)), 6.42 (dd, J = 6.5, 3.3 Hz, 1H (isomer B)), 5.15 (dd, J = 12.7, 10.5 Hz, 1H (isomer A)), 5.05 (dt, J = 10.4, 8.0 Hz, 1H (both isomer)), 4.95 (dd, J = 10.4, 5.6 Hz, 1H (isomer B)), (m, 1H(both isomer)), (m, 1H(both isomer)), 3.33 (dd, J = 17.6, 10.6 Hz, 1H (both isomer)), 3.05 (dd, J = 23.4, 14.9 Hz, 1H (both isomer)), 1.55 (t, J = 4.8 Hz, 3H (both isomer)), 1.41 (d, J = 1.0 Hz, 9H (both isomer)). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (d, J = 52.5 Hz), (d, J = 53.3 Hz), (d, J = 2.2 Hz), (d, J = 2.1 Hz), (d, J = 4.5 Hz), (d, J = 4.5 Hz), (d, J = 14.4 Hz), (d, J = 15.8 Hz), (d, J = Hz), (d, J = Hz), (s), (s), (s), (s), (d, J = 1.6 Hz), (d, J = 1.5 Hz), (d, J = 2.5 Hz), (d, J = 3.2 Hz), (d, J = 5.4 Hz), (d, J = 6.0 Hz), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (dd, J = 13.0, 6.9 Hz, 1F (isomer A)), (dd, J = 12.1, 7.0 Hz, 1F (isomer B)), (t, J = 47.0 Hz, 2F (isomer A), (t, J = 47.0 Hz, 2F (isomer B)). HRMS (ESI) calcd for C 16 H 22 F 2 4 S + (M+H + ): , found: tert-butyl-7-fluoro-4-methyl-4-((2,2,2-trifluoroethylsulfonyl)methyl)-2-azaspiro[4.5]deca-6,9-diene-3,8- dione (7k) Prepared according to general method and isolated in 76% yield after chromoatography as yellow oil (62.6 mg): 1 H MR (500 MHz, CDCl 3 ) F S 2 CH 2 CF 3 δ 6.91 (ddd, J = 9.7, 6.8, 2.8 Hz, 1H (both isomers)), (m, 2H (both isomers)), (m, 1H (isomer A)), 3.85 (dq, J = 18.5,
20 Hz, 1H (isomer B), (m, 2H (both isomers)), 3.32 (dd, J = 14.2, 10.7 Hz, 1H(both isomers)), 3.12 (dd, J = 33.4, 14.9 Hz, 1H(both isomers)), 1.55 (d, J = 2.3 Hz, 3H(both isomers)), 1.40 (d, J = 0.7 Hz, 9H (both isomers)). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (d, J = 55.7 Hz), (d, J = 56.5 Hz), (s), (s), (s), (d, J = 4.2 Hz), δ (d, J = Hz), (d, J = Hz), (q, J = Hz), (s), (q, J = 31.6 Hz), (q, J = 31.8 Hz), (s), (s), (s), (s), (d, J = 1.7 Hz), (d, J = 2.7 Hz), (d, J = 5.2 Hz), (d, J = 6.0 Hz), (s), (d, J = 11.5 Hz). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 9.3 Hz, 2F (isomer A)), (t, J = 9.2 Hz, 2F (isomer B)), (dd, J = 13.0, 6.9 Hz, 1F (isomer A)), (dd, J = 12.8, 6.9 Hz, 2F (isomer B)). HRMS (ESI) calcd for C 17 H 22 F 4 4 S + (M+H + ): , found: tert-butyl-4-((fluoromethylsulfonyl)methyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (6q) Prepared according to general method and isolated in 82% yield after chromoatography as yellow oil (54.1 mg): 1 H MR (500 MHz, CDCl 3 ) δ S 2 CH 2 F 6.86 (dd, J = 9.9, 2.9 Hz, 1H), 6.77 (dd, J = 10.1, 3.0 Hz, 1H), 6.45 (td, J = 11.9, 1.8 Hz, 2H), 5.56 (dd, J = 46.6, 10.1 Hz, 1H), (m, 1H), 3.67 (d, J = 10.3 Hz, 1H), 3.54 (dd, J = 15.4, 7.4 Hz, 1H), 3.38 (dd, J = 7.4, 4.0 Hz, 1H), 3.34 (d, J = 10.3 Hz, 1H), 2.50 (dd, J = 15.2, 3.4 Hz, 1H), 1.41 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (d, J = Hz), (s), (s), (s), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 46.6 Hz). HRMS (ESI) calcd for C 15 H 21 F 4 S + (M+H + ): , found: tert-butyl-4-((2,2,2-trifluoroethylsulfonyl)methyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione (7q) Prepared according to general method and isolated in 83% yield after chromoatography as yellow oil (63.0 mg): 1 H MR (500 MHz, CDCl 3 ) δ S 2 CH 2 CF (dd, J = 10.0, 3.1 Hz, 1H), 6.78 (dd, J = 10.1, 3.1 Hz, 1H), 6.49 (dd, J = 10.0, 1.8 Hz, 1H), 6.46 (dd, J = 10.1, 1.8 Hz, 1H), 4.63 (dq, J = 18.3, 9.1 Hz, 1H), (m, 1H), 3.69 (d, J = 10.3 Hz, 1H), 3.55 (dd, J = 15.3, 8.2 Hz, 1H), 3.43 (dd, J = 8.2, 3.1 Hz, 1H), 3.37 (d, J = 10.3 Hz, 1H), 2.55 (dd, J = 15.3, 2.2 Hz, 1H), 1.44 (s, 9H). 13 C MR (126 MHz, CDCl 3 ) δ (s), (s), (s), (s), (s), (s), (q, J = Hz), (q, J = 31.6 Hz), (s), (s), (s), (s), (s), (s). 19 F MR (282 MHz, CDCl 3 ) δ (t, J = 9.2 Hz). HRMS (ESI) calcd for C 16 H 21 F 3 4 S + (M+H + ): , found:
21 IV. References 1. Han, G.; Liu, Y.; Wang, Q. rg. Lett. 2014, 16, Tang, X.J.; Thomoson, C.S.; Dolbier, W. R. Jr. rg. Lett. 2014, 16,
22 V. MR Spectra for new compounds 22
23 Me 1a 23
24 Me 1a 24
25 Bn 1b 25
26 Bn 1b 26
27 PMB 1c 27
28 PMB 1c 28
29 Bn 1d 29
30 Bn 1d 30
31 Bn 1e 31
32 Bn 1e 32
33 Bn 1f 33
34 Bn 1f 34
35 Bn 1g 35
36 Bn 1g 36
37 Bn Bn 1h 37
38 Bn Bn 1h 38
39 Bn 1i 39
40 Bn 1i 40
41 Me Bn 1j 41
42 Me Bn 1j 42
43 F Bn 1k 43
44 F Bn 1k 44
45 F Bn 1k 45
46 46
47 Cl Bn 1l 47
48 Cl Bn 1l 48
49 Br Bn 1m 49
50 Br Bn 1m 50
51 tbu Bn 1n 51
52 tbu Bn 1n 52
53 Me Bn Me 1o 53
54 Me Bn Me 1o 54
55 tbu Bn 1p 55
56 tbu Bn 1p 56
57 Bn 1q 57
58 Bn 1q 58
59 CF 2 H 2a 59
60 CF 2 H 2a 60
61 CF 2 H 2a 61
62 2d CF 2 H 62
63 2d CF 2 H 63
64 2d CF 2 H 64
65 2e CF 2 H 65
66 2e CF 2 H 66
67 2e CF 2 H 67
68 CF 2 H 2f 68
69 CF 2 H 2f 69
70 CF 2 H 2f 70
71 2g CF 2 H 71
72 2g CF 2 H 72
73 2g CF 2 H 73
74 Bn HF 2 C 2g' 74
75 Bn HF 2 C 2g' 75
76 Bn HF 2 C 2g' 76
77 2h CF 2 H 77
78 2h CF 2 H 78
79 2h CF 2 H 79
80 Me 2j CF 2 H 80
81 Me 2j CF 2 H 81
82 Me 2j CF 2 H 82
83 F 2k CF 2 H 83
84 F 2k CF 2 H 84
85 F 2k CF 2 H 85
86 Cl 2l CF 2 H 86
87 Cl 2l CF 2 H 87
88 Cl 2l CF 2 H 88
89 Br 2m CF 2 H 89
90 Br 2m CF 2 H 90
91 Br 2m CF 2 H 91
92 CF 2 H 2n 92
93 CF 2 H 2n 93
94 CF 2 H 2n 94
95 Me Me 2o CF 2 H 95
96 Me Me 2o CF 2 H 96
97 Me Me 2o CF 2 H 97
98 2p CF 2 H 98
99 2p CF 2 H 99
100 2p CF 2 H 100
101 2q CF 2 H 101
102 2q CF 2 H 102
103 2q CF 2 H 103
104 3 CF 2 CEt 104
105 3 CF 2 CEt 105
106 3 CF 2 CEt 106
107 4 CF 3 107
108 4 CF 3 108
109 4 CF 3 109
110 5 CF 2 CF 2 CF 2 CF 3 110
111 5 CF 2 CF 2 CF 2 CF 3 111
112 5 CF 2 CF 2 CF 2 CF 3 112
113 6a S 2 CH 2 F 113
114 6a S 2 CH 2 F 114
115 6a S 2 CH 2 F 115
116 7a S 2 CH 2 CF 3 116
117 7a S 2 CH 2 CF 3 117
118 7a S 2 CH 2 CF 3 118
119 6f S 2 CH 2 F 119
120 6f S 2 CH 2 F 120
121 6f S 2 CH 2 F 121
122 7f S 2 CH 2 CF 3 122
123 7f S 2 CH 2 CF 3 123
124 7f S 2 CH 2 CF 3 124
125 Me S 2 CH 2 F 6j 125
126 Me S 2 CH 2 F 6j 126
127 Me S 2 CH 2 F 6j 127
128 Me 7j S 2 CH 2 CF 3 128
129 Me 7j S 2 CH 2 CF 3 129
130 Me 7j S 2 CH 2 CF 3 130
131 F 6k S 2 CH 2 F 131
132 F 6k S 2 CH 2 F 132
133 F 6k S 2 CH 2 F 133
134 F 7k S 2 CH 2 CF 3 134
135 F 7k S 2 CH 2 CF 3 135
136 F 7k S 2 CH 2 CF 3 136
137 6q S 2 CH 2 F 137
138 6q S 2 CH 2 F 138
139 6q S 2 CH 2 F 139
140 7q S 2 CH 2 CF 3 140
141 7q S 2 CH 2 CF 3 141
142 7q S 2 CH 2 CF 3 142
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Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
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