Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
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1 Supplementary information for the paper Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Yang Xue, Ling-Po Li, Yan-Hong He * & Zhi Guan * School of Chemistry and Chemical Engineering, Southwest University, Chongqing, , P. R. China Fax: ; guanzhi@swu.edu.cn for Z. Guan, heyh@swu.edu.cn for Y-H He Contents 1. Reaction profiles of the SGP-catalysed Mannich reaction and the blank reaction 2. Optimisation of reaction conditions for the SGP-catalysed Mannich reaction 3. Characterization of the Mannich products 4. 1 H NMR, 13 C NMR and HPLC spectra for the Mannich products 4a-4r 5. HPLC spectra for reaction profiles of the SGP-catalysed the Mannich reaction and the blank reaction 6. References 1. Reaction profiles of the SGP-catalysed Mannich reaction and the blank reaction. Supplementary Table S1. Reaction profile of the blank reaction a. Entry Time (h) Yield (%) b dr (syn:anti) c 1 6 no observed trace : : : : : : :59 a Reaction conditions: a mixture of 4-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone (5 mmol), deionised water (0.10 ml), MeCN (0.9 ml) was stirred at 30 C for 6-96 h. b Yield of the isolated product after silica gel chromatography. c Determined by chiral HPLC analysis. 1
2 Supplementary Table S2. Reaction profile of the SGP-catalysed Mannich reaction a. Entry Time (h) Yield (%) b dr (syn:anti) c e.e. (syn) (%) d : : : : : : : : :9 84 a Reaction conditions: a mixture of 4-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone (5 mmol), deionised water (0.10 ml), MeCN (0.9 ml) and SGP (50 mg) was stirred at 30 C for 6-96 h. b Yield of the isolated product after silica gel chromatography. c Determined by chiral HPLC analysis. d e.e. value of the syn-isomer, determined by chiral HPLC using a chiralpak AD-H column. 2. Optimisation of reaction conditions for the SGP-catalysed Mannich reaction. Supplementary Table S3. Influence of water content on the SGP-catalysed Mannich reaction a. Entry Water content (%) Yield (%) b dr (syn:anti) c e.e. (syn) (%) d : : : : : : : :22 73 a Reaction conditions: a mixture of 4-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone (5 mmol), deionised water [0-0.35, H 2 O / (H 2 O + MeCN), v/v], MeCN (H 2 O + MeCN = 1mL) and SGP (50 mg) was stirred at 30 C for 96 h. b Yield of the isolated product after silica gel chromatography. c Determined by chiral HPLC analysis. d e.e. value of the syn-isomer, determined by chiral HPLC using a chiralpak AD-H column. Supplementary Table S4. Effect of ph on the SGP-catalysed Mannich Reaction a. Entry ph Yield (%) b dr (syn:anti) c e.e. (syn) (%) d :
3 : : : :11 82 a Reaction conditions: a mixture of 4-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone (5 mmol), a phosphate buffer (NaH 2 PO 4 -Na 2 HPO 4, 0.2 M, ph , 0.1 ml), MeCN (0.9 ml) and SGP (50 mg) was stirred at 30 C for 96 h. b Yield of the isolated product after silica gel chromatography. c Determined by chiral HPLC analysis. d e.e. value of the syn-isomer, determined by chiral HPLC using a chiralpak AD-H column. Supplementary Table S5. Effect of molar ratio of substrates on the SGP-catalysed Mannich reaction a. Entry Molar ratio b Yield (%) c dr (syn:anti) d e.e. (syn) (%) e 1 1: : : : : : : : : :12 82 a Reaction conditions: a mixture of 4-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone ( mmol), deionised water (0.10 ml), MeCN (0.9 ml) and SGP (50 mg) was stirred at 30 C for 96 h. b Molar ratio of cyclohexanone to 4-nitrobenzaldehyde. c Yield of the isolated product after silica gel chromatography. d Determined by chiral HPLC analysis. e e.e. value of the syn-isomer, determined by chiral HPLC using a chiralpak AD-H column. Supplementary Table S6. Influence of temperature on the SGP-catalysed Mannich reaction a. Entry T ( C) Yield (%) b dr (syn:anti) c e.e. (syn) (%) d : : : : : : :31 75 a Reaction conditions: a mixture of 4-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone (0.75 mmol), deionised water (0.10 ml), MeCN (0.9 ml) and SGP (50 mg) was stirred at C for 96 h. b Yield of the isolated product after silica gel chromatography. c Determined by chiral HPLC analysis. d e.e. value of the syn-isomer, determined by chiral HPLC using a chiralpak AD-H column. Supplementary Table S7. Time course of the SGP-catalysed Mannich Reaction a. Entry Time (h) Yield (%) b dr (syn:anti) c e.e. (syn) (%) d 3
4 : : : : : : : :21 76 a Reaction conditions: a mixture of 4-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone (7.5 mmol), deionised water (0.10 ml), MeCN (0.9 ml) and SGP (50 mg) was stirred at 30 C for h. b Yield of the isolated product after silica gel chromatography. c Determined by chiral HPLC analysis. d e.e. value of the syn-isomer, determined by chiral HPLC using a chiralpak AD-H column. 3. Characterization of the Mannich products O NO 2 2-[(4-nitrophenyl)(phenylamino)methyl]yclohexanone (syn) 1 (4a) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 210.6, 149.6, 147.0, 146.6, 129.1, 128.6, 123.6, 118.3, 114.0, 57.1, 56.2, 42.4, 29.0, 27.0, 24.9 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 80:20, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O CF 3 2-[(phenylamino)(4-(trifluoromethyl)phenyl)methyl]cyclohexanone (syn) 1 (4b) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 4H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), (m, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR 4
5 (75 MHz, CDCl 3 ): δ = 210.9, 146.9, 145.8, 129.1, 127.9, 125.3, 125.3, 118.0, 114.0, 57.1, 56.3, 42.4, 28.8, 27.0, 24.9 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AS-H, hexane/isopropanol = 90:10, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O Br 2-[(4-bromophenyl)(phenylamino)methyl]cyclohexanone (syn) 1 (4c) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), (m, 2H), (m,1h), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.1, 147.1, 140.5, 131.4, 129.4, 129.0, 120.8, 117.9, 114.0, 56.9, 56.3, 42.4, 28.8, 27.0, 24.8 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 95:5, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O Cl 2-[(4-chlorophenyl)(phenylamino)methyl]cyclohexanone (syn) 1 (4d) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 4H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), (m, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.2, 147.1, 140.0, 132.6, 129.0, 129.0, 128.5, 117.9, 114.0, 56.9, 56.3, 42.4, 28.9, 27.0, 24.8 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 95:5, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). 5
6 O F 2-[(3-fluorophenyl)(phenylamino)methyl]cyclohexanone (syn) 1 (4e) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 3H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), (m, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.0, 161.4, 147.2, 144.6, 129.8, 129.7, 129.0, 123.1, 117.9, 114.0, 113.8, 56.9, 56.4, 42.4, 28.6, 27.0, 24.8 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralcel OJ-H, hexane/isopropanol = 85:15, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O F 2-[(4-fluorophenyl)(phenylamino)methyl]cyclohexanone (syn) 2 (4f) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 3H), (m, 2H), (m, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.3, 160.1, 147.2, 137.0, 129.1, 117.8, 115.3, 114.0, 56.8, 56.4, 42.4, 28.9, 27.0, 24.8 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 90:10, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O CN 4-[(2-oxocyclohexyl)(phenylamino)methyl]benzonitrile (syn) 1 (4g) H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H),
7 (m, 1H), (m, 2H), (m, 2H), (m, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.9, 147.7, 146.7, 132.2, 129.2, 128.1, 118.8, 117.9, 113.4, 110.8, 57.8, 57.0, 42.3, 31.9, 27.8, 24.4 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AS-H, hexane/isopropanol = 80:20, flow rate 0.5 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O 2-[phenyl(phenylamino)methyl]cyclohexanone (syn) 2 (4h) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 5H), (m, 2H), (m, 3H), (m, 2H), (m, 1H), (m, 2H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.3, 147.4, 141.5, 129.0, 128.3, 127.5, 117.6, 114.0, 57.2, 56.6, 42.4, 28.6, 27.0, 24.8 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 90:10, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O CH 3 2-[4-methyl-phenyl(phenylamino)methyl]cyclohexanone (syn) 2 (4i) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 4H), (m, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), 2.29 (s, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.5, 147.5, 138.4, 136.5, 129.0, 129.0, 127.4, 117.5, 114.0, 56.9, 56.6, 42.4, 28.7, 27.0, 24.8, 21.0 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 95:5, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). 7
8 Br O NO 2 2-[(3-bromophenylamino)-(4-nitrophenyl)methyl]cyclohexanone (syn) 3 (4j) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 2H), (m, 2H), (m, 4H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 210.5, 148.7, 148.3, 147.2, 130.4, 128.5, 123.7, 121.1, 116.7, 112.4, 57.0, 42.3, 32.0, 29.0, 26.9, 24.8 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 85:15, flow rate 0.5 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). CH 3 O NO 2 2-[(3-Methylphenylamino)-(4-nitrophenyl)methyl]cyclohexanone (syn) 3 (4k) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 1H), (m, 1H), 6.36 (s, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 2H), 2.19 (s, 3H), (m, 6H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 210.6, 149.7, 138.9, 128.5, 123.6, 119.3, 114.9, 110.9, 57.1, 56.2, 42.4, 29.0, 27.0, 24.9, 21.5 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 85:15, flow rate 1 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). Cl O NO 2 8
9 2-[(4-Chlorophenylamino)-(4-nitrophenyl)methyl]cyclohexanone (syn) 3 (4l) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 6H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 210.6, 149.1, 149.0, 147.1, 128.9, 128.5, 123.6, 123.4, 114.6, 57.3, 56.7, 42.4, 27.8, 24.7 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 85:15, flow rate 1 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). CH 3 O NO 2 2-[(4-Methylphenylamino)-(4-nitrophenyl)methyl]cyclohexanone (syn) 3 (4m) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), 2.17 (s, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 210.7, 149.8, 147.0, 129.6, 128.6, 127.6, 123.6, 113.6, 57.4, 57.0, 42.4, 29.0, 27.1, 24.9, 20.3 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 80:20, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). OCH 3 O NO 2 2-[(4-methoxy-phenylamino)-(4-nitro-phenyl)-methyl]-cyclohexanone (syn) 1 (4n) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 1H), 4.29 (br, 1H), 3.67 (s, 3H), (m, 3H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 210.8, 152.6, 149.9, 147.0, 140.7, 128.5, 123.6, 115.6, 114.6, 58.0, 56.3, 55.6, 42.4, 31.8, 27.1, 24.9 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 75:25, flow rate 0.5 ml/min, λ 9
10 = 254 nm), syn-diastereomer: t R = min (minor), min (major). OCH 3 O Br 2-[(4-methoxyphenylamino)-(4-bromophenyl)methyl]cyclohexanone (syn) 4 (4o) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 1H), 4.33 (br, 1H), 3.67 (s, 3H), (m, 1H), (m, 2H), (m, 3H), (m, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 211.3, 152.4, 141.0, 140.8, 131.4, 129.4, 120.7, 115.6, 114.7, 57.8, 56.4, 55.6, 42.4, 28.6, 27.1, 24.9 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AS-H, hexane/isopropanol = 80:20, flow rate 0.5 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O S Cl 3-[(4-chlorophenyl)(phenylamino)methyl]dihydro-2H-thiopyran-4(3H)-one (syn) 1 (4p) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 6H), (m, 1H), (m, 2H), (m, 1H), 4.44 (s, 1H), (m, 3H), (m, 2H), (m, 2H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 208.5, 146.6, 139.2, 133.2, 129.2, 128.9, 128.6, 118.4, 114.1, 58.4, 57.2, 44.2, 31.7, 30.3 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralcel OD-H, hexane/isopropanol = 95:5, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). O S CF 3 10
11 3-[(phenylamino)(4-(trifluoromethyl)phenyl)methyl]dihydro-2H-thiopyran-4(3H)-one (syn) 1 (4q) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 4H), (m, 2H), (m, 1H), (m, 2H), (m, 1H), 4.49 (s, 1H), (m, 1H), (m, 4H), (m, 2H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 208.2, 146.4, 144.9, 129.9, 129.2, 127.6, 125.7, 125.7, 118.5, 114.1, 58.4, 57.4, 44.3, 31.6, 30.3 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AS-H, hexane/isopropanol = 90:10, flow rate 1.0 ml/min, λ = 254 nm), syn-diastereomer: t R = min (minor), min (major). OCH 3 O NO 2 4-(4-methoxyphenylamino)-4-(4-nitrophenyl)butan-2-one 5 (4r) 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 1H), (m, 1H), 3.69 (s, 3H), (m, 2H), 2.15 (s, 3H) ppm; 13 C NMR (75 MHz, CDCl 3 ): δ = 206.0, 152.8, 150.6, 147.2, 140.1, 127.4, 124.0, 115.4, 114.8, 55.6, 54.6, 50.6, 30.6 ppm; The enantiomeric excess was determined by HPLC (Daicel Chiralpak AD-H, hexane/isopropanol = 50:50, flow rate 0.5 ml/min, λ = 280 nm), t R (S) = min, t R (R) = min H NMR, 13 C NMR and HPLC spectra of the Mannich products 4a-4r 1 H NMR Spectrum (CDCl 3 ) of 4a 11
12 13 C NMR Spectrum (CDCl 3 ) of 4a 1 H NMR Spectrum (CDCl 3 ) of 4b 12
13 13 C NMR Spectrum (CDCl 3 ) of 4b 1 H NMR Spectrum (CDCl 3 ) of 4c 13
14 13 C NMR Spectrum (CDCl 3 ) of 4c 1 H NMR Spectrum (CDCl 3 ) of 4d 14
15 13 C NMR Spectrum (CDCl 3 ) of 4d 1 H NMR Spectrum (CDCl 3 ) of 4e 15
16 13 C NMR Spectrum (CDCl 3 ) of 4e 1 H NMR Spectrum (CDCl 3 ) of 4f 16
17 13 C NMR Spectrum (CDCl 3 ) of 4f 1 H NMR Spectrum (CDCl 3 ) of 4g 17
18 13 C NMR Spectrum (CDCl 3 ) of 4g 1 H NMR Spectrum (CDCl 3 ) of 4h 18
19 13 C NMR Spectrum (CDCl 3 ) of 4h 1 H NMR Spectrum (CDCl 3 ) of 4i 19
20 13 C NMR Spectrum (CDCl 3 ) of 4i 1 H NMR Spectrum (CDCl 3 ) of 4j 20
21 13 C NMR Spectrum (CDCl 3 ) of 4j 1 H NMR Spectrum (CDCl 3 ) of 4k 21
22 13 C NMR Spectrum (CDCl 3 ) of 4k 1 H NMR Spectrum (CDCl 3 ) of 4l 22
23 13 C NMR Spectrum (CDCl 3 ) of 4l 1 H NMR Spectrum (CDCl 3 ) of 4m 23
24 13 C NMR Spectrum (CDCl 3 ) of 4m 1 H NMR Spectrum (CDCl 3 ) of 4n 24
25 13 C NMR Spectrum (CDCl 3 ) of 4n 1 H NMR Spectrum (CDCl 3 ) of 4o 25
26 13 C NMR Spectrum (CDCl 3 ) of 4o 1 H NMR Spectrum (CDCl 3 ) of 4p 26
27 13 C NMR Spectrum (CDCl 3 ) of 4p 1 H NMR Spectrum (CDCl 3 ) of 4q 27
28 13 C NMR Spectrum (CDCl 3 ) of 4q 1 H NMR Spectrum (CDCl 3 ) of 4r 28
29 13 C NMR Spectrum (CDCl 3 ) of 4r HPLC Spectra of the Mannich Products 29
30 O NO 2 (4a) 4a (Racemic) Sum a (Chiral) Sum
31 O CF 3 (4b) 4b (Racemic) Sum b (Chiral) Sum
32 O Br (4c) 4c (Racemic) Sum c (Chiral) Sum
33 O Cl (4d) 4d (Racemic) Sum d (Chiral) Sum
34 O F (4e) 4e (Racemic) Sum e (Chiral) Sum
35 O F (4f) 4f (Racemic) Sum f (Chiral) Sum
36 O CN (4g) 4g (Racemic) Sum g (Chiral) Sum
37 O (4h) 4h (Racemic) Sum h (Chiral) Sum
38 O CH 3 (4i) 4i (Racemic) Sum i (Chiral) Sum
39 Br O 4j (Racemic) NO 2 (4j) Sum j (Chiral) Sum
40 CH 3 O 4k (Racemic) NO 2 (4k) Sum k (Chiral) Sum
41 Cl O 4l (Racemic) NO 2 (4l) Sum l (Chiral) Sum
42 CH 3 O 4m (Racemic) NO 2 (4m) Sum m (Chiral) Sum
43 OCH 3 O 4n (Racemic) NO 2 (4n) Sum n (Chiral) Sum
44 OCH 3 O Br (4o) 4o (Racemic) Sum o (Chiral) Sum
45 O S Cl (4p) 4p (Racemic) Sum p (Chiral) Sum
46 O S CF 3 (4q) 4q (Racemic) Sum q (Chiral) Sum
47 OCH 3 O 4r (Racemic) NO 2 (4r) Sum r (Chiral) Sum
48 5. HPLC spectra of reaction profiles of the SGP-catalysed the Mannich reaction and the blank reaction. 5.1 HPLC Spectra of Table S1 Entry Sum Entry
49 Sum Entry Sum Entry
50 Sum Entry Sum Entry
51 Sum Entry Sum HPLC Spectra of Table S2 Entry
52 Sum Entry Sum Entry
53 Sum Entry Sum Entry
54 Sum Entry Sum Entry
55 Sum Entry Sum Entry
56 Sum References 1. Guo, Q.X., Liu, H., Guo, C., Luo, S.W., Gu, Y., Gong, L.Z. Chiral Brønsted acid-catalyzed direct asymmetric Mannich Reaction. J. Am. Chem.Soc. 129, (2007). 2. Zheng, X., Qian, Y.B., Wang, Y.M. 2-Pyrrolidinecarboxylic acid ionic liquid as a highly efficient organocatalyst for the asymmetric one-pot Mannich reaction. Eur. J. Org. Chem. 2010, (2010). 3. An, Y.-J., Wang, C.-C., Liu, Z.-P., Tao, J.-C. Isosteviol-proline conjugates as highly efficient amphiphilic organocatalysts for asymmetric three-component Mannich reactions in the presence of water. Helv. Chim. Acta 95, (2012). 4. Ibrahem, I., Zou, W.B., Engqvist, M., Xu, Y.M., Cordova, A. Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction. Chem. Eur. J. 11, (2005). 5. List, B., Pojarliev, P., Biller, W.T., Martin, H.J. The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization and application to the highly enantioselective synthesis of 1,2-amino alcohols. J. Am. Chem. Soc. 124, (2002). 56
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Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
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Xiangya International Academy of Translational Medicine, Central South University, 172 Tongzipo Rd., Changsha, Hunan province, China,
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SUPPLEMETARY IFRMATI DI: 10.1038/CEM.1406 ighly enantioselective trapping of zwitterionic intermediates by imines uang Qiu,a, Ming Li,a, Li-Qin Jiang a, Feng-Ping Lv a, Li Zan a, Chang-Wei Zhai a, Michael.
Supplementary Figure 1. (X-ray structures of 6p and 7f) O N. Br 6p
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DOI: 10.1038/NCHEM.1998 An organic thiyl radical catalyst for enantioselective cyclization Takuya Hashimoto, Yu Kawamata and Keiji Maruoka Department of Chemistry, Graduate School of Science, Kyoto University,
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Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,
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ELECTRONIC SUPPORTING INFORMATION Ermal Ismalaj a, Giacomo Strappaveccia a, Eleonora Ballerini a, Fausto Elisei a, Oriana Piermatti a, Dmitri Gelman b, Luigi Vaccaro a a CEMIN - Dipartimento di Chi mica,