Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
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1 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
2 Rhodium-Catalyzed Cyclopropanation of Alkenes with Diazomalonates Francisco González-Bobes, a * Michaël D. B. Fenster, a Susanne Kiau, a Laxma Kolla, a Sergei Kolotuchin, a Maxime Soumeillant a a Process Research and Development, Bristol-Myers Squib, Research and Development, One Squibb Drive, P.O. Box 191, New Brunswick, New Jersey francisco.gonzalezbobes@bms.com Supporting Information I. General The following chemicals were purchased and used as received: dimethyldimalonate (Alfa Aesar), diethylmalonate (Alfa Aesar), Rh2(esp)2 (Aldrich), dichlomethane (anhydrous, EMD), pentafluorostyrene (Alfa Aesar), 4-acetamidobenzenesulfonyl azide (Aldrich, Alfa Aesar), Rh2(OAc)4 (Aldrich), Rh2(TFA)4 (Aldrich), Rh2(TPA)4 (TCI), styrene (Alfa Aesar), 2-fluorostyrene (Alfa Aesar), 2,5-difluorostyrene (Alfa Aesar), 4-trifluoromethylstyrene (Alfa Aesar), 4-fluorostyrene (Alfa Aesar), 4-chlorostyrene (Alfa Aesar), vinylferrocene (Strem), 4-methoxystyrene (Alfa Aesar), 2-methoxystyrene (Aldrich), 4-cyanostyrene (Alfa Aesar), 3-bromostyrene (Alfa Aesar), 2-bromostyrene (Alfa Aesar), 5-hexenenitrile (Alfa Aesar), 3-butenenitrile (Alfa Aesar), 1-octene (Alfa Aesar), allylbutylether (Aldrich), allylphenylether (Aldrich), allylbenzylether (Alfa Aesar), 4-phenyl-1-butene (Alfa Aesar), 3,3-dimethyl-1-hexene (TCI), cycloheptene (TCI), 1,2-dihydronaphthalene (Aldrich), indene (Aldrich), (Z)-1,3-dichloro-1-propene (TCI), (Z)-β-methylstyrene (GFS), (E)-β-methylstyrene (Aldrich), (Z)-4-octene (Alfa Aesar), (E)-4-octene (Alfa Aesar), 1-phenylpropyne (Avocado), thiourea (Alfa Aesar). Diazo dimethylmalonate and diazo diethylmalonate were prepared as previously reported. 1 1 Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, P1
3 II. Cyclopropanation reactions General Protocol (Table 2, Table 3 and Scheme 2). In the air, Rh2(esp)2 (2 mg, 2.5 µmol, 0.1 mol %) was placed in a 100 ml threenecked flask equipped with a stir bar. The flask was capped and purged with nitrogen (three vacuum/refilling cycles). DCM (2.5 ml) was added by syringe leading to a pale green homogenous solution. The alkene (2.5 mmol, 1 equiv) was added and the reaction mixture was then cooled in a water/ice bath. After 5 minutes, a solution of diazodimethylmalonate (514 mg, 3.25 mmol, 1.3 equiv) in DCM (2.5 mmol) was added by syringe. 2 The resulting solution was kept in the bath for 10 min and then stirred at room temperature. After 2 hours, the reaction mixture was treated with a saturated solution of aqueous thiourea (50 ml) and diluted with 25 ml of DCM. The mixture was stirred for 30 minutes and then transferred into a separatory funnel. The aqueous layer was extracted with DCM (3 x 25 ml). The combined organic layers were washed with brine (100 ml), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was then purified by column chromatography on silica gel with the solvent systems indicated. MeO 2 C Dimethyl 2-phenylcyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: 9:1 hexanes:ethyl acetate. Colorless oil. 542 mg (93 %). 1H NMR (300 MHz, CDCl 3 ) δ (5H, m), 3.81 (3H, s ), 3.37 (3H, s), 3.25 (1H, t, J = 8.5 Hz), 2.21 (1H, dd, J = 7.8, 5.4 Hz), 1.76 (1H, dd, J = 9.3, 5.4 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 170.2, 167.0, 134.5, 128.4, 128.4, 128.1, 128.1, 127.3, 52.7, 52.1, 37.2, 32.5, IR (neat) cm , 1729, MS (CI) calcd for C 13 H 14 O 4 : 234 found: Nitrogen evolution is observed. P2
4 MeO 2 C CO2 Me F Dimethyl 2-(2-fluorophenyl) cyclopropane-1,1-dicarboxylate (Table 2). Reaction was run at 5 mmol scale. Solvent used for chromatography: Gradient from 9:1 to 6:1 hexanes: ethyl acetate. Colorless oil g (91 %). 1H NMR (300 MHz, CDCl 3 ) δ 7.25 (1H, m), 7.03 (3H, m), 3.78 (3H, s), 3.37 (3H, m), 3.26 (1H, t, J = 8.7 Hz), 2.19 (1H, dd, J = 8.4, 5.1 Hz), 1.77 (1H, dd, J= 9.1, 5.1 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.4, 166.6, (d, 1 J C-F = 246 Hz ), (d, 3J C-F = 8 Hz), (d, 4 J C-F = 3.0 Hz), (d, 3 J C-F = 3.6 Hz), (d, 2 J C-F = 14 Hz), (d, 2 J C-F = 21 Hz), 53.3, 52.8, 37.0, 27.2, IR (neat) cm , 1731, 1495, MS (CI) calcd for C 13 H 13 FO 4 : 252, found: 253. MeO F 2 C F Dimethyl 2-(2,5-difluorophenyl)cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: 12:1 hexanes:ethyl acetate. Colorless oil. 652 mg (93%). 1H NMR (300 MHz, CDCl 3 ) δ (1H, m), (2H, m), 3.78 (3H, s), 3.45 (3H, s), 2.95 (1H, t, J = 8.8 Hz), 2.84 (1H, dd, J = 8.5, 5.2 Hz), 1.85 (1H, dd, J = 9.2, 5.2 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.7, 169.4, (d, 1 J C-F = 250 Hz), (d, 1J C-F = 250 Hz), (4C, m), 52.8, 52.3, 34.5, 22.5, 20.4 IR (neat) cm , 1731, 1627, 1589, 1468, MS (CI) calcd for C 13 H 12 F 2 O 4 : 270, found: 271. P3
5 MeO 2 C F 3 C Dimethyl 2-(4-(trifluoromethyl)phenyl)cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: 9:1 hexanes:ethyl acetate. Colorless oil. 731 mg (97 %). 1H NMR (300 MHz, CDCl 3 ) δ 7.50 (2H, d, J = 8.2 Hz), 7.29 (2H, d, J = 8.2 Hz), 3.78 (3H, s), 3.36 (3H, s), 3.23 (1H, t, J = 8.7 Hz), 2.19 (1H, dd, J = 8.3, 5.3 Hz), 1.77 (1H, dd, J = 9.1, 5.3 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.8, 166.6, 138.8, (q, 2 J C-F = 32), 128.8, (q, 3 J C-F = 3.8 Hz), (q, 1 J C-F = 272 Hz), 52.9, 52.3, 37.3, 31.7, IR (neat) cm , 1731, 1620, MS (CI) calcd for C 14 H 13 F 3 O 4 : 302 found: 303. EtO 2 C CO2 Et F Diethyl 2-(4-fluorophenyl)cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: Gradient from 13:1 to 6:1 hexanes:ethyl acetate. Colorless oil. 612 mg (90 %). 1H NMR (300 MHz, CDCl 3 ) δ (2H, m), (2H, m), (2H, m), (2H, m), 3.15 (1H, t, J = 8.6 Hz), 2.08 (1H, dd, J = 8.0, 5.1 Hz), 1.66 (1H, dd, J = 9.2, 5.1 Hz), 1.26 (3H, t, J = 7.1 Hz), 0.87 (3H, t, J = 7.1 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.6, 166.4, (d, 1 J C-F = 246), (d, 4 J C-F = 2.8), (d, 3 J C-F = 8.1 Hz), (d, 2 J C-F = 21 Hz), 61.6, 61.1, 37.2, 31.2, 18.7, 14.0, IR (neat) cm , 1726, 1607, MS (CI) calcd for C 15 H 17 FO 4 : 280, found: 281. F MeO F 2 C F F F Dimethyl 2-(perfluorophenyl)cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: 10:1 hexanes:ethyl acetate. Colorless oil. 760 mg (94 %). P4
6 1H NMR (300 MHz, CDCl 3 ) δ 3.78 (3H, s), 3.57 (3H, s), 2.87 (1H, t, J = 8.4 Hz), 2.20 (1H, dd, J = 7.7, 5.4 Hz), 1.89 (1H, t, J = 9.0, 5.4 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 168.9, 167.3, (5C, m), (ddd, 2 J C- F = 19, 3 J C-F = 15, 4 J C-F = 3.8 Hz), 53.0, 52.7, 34.1, 21.3 (d, 4 J C-F = 1.1 Hz), 20.0 (t, 3J C-F = 4.4 Hz). IR (neat) cm , 1732, 1657, 1439, MS (CI) calcd for C 13 H 9 F 5 O 4 : 324 found: 325. MeO 2 C CO2 Me Cl Dimethyl 2-(4-chlorophenyl) cyclopropane-1, 1-dicarboxylate (Table 2). Reaction was run at 5 mmol scale. Solvent used for chromatography: Gradient from 9:1 to 6:1 hexanes:ethyl acetate. Colorless oil g (90 %). 1H NMR (400 MHz, CDCl 3 ) δ 7.23 (2H, d, J = 8.0 Hz), 7.19 (2H, d, J = 8.0 Hz), 3.77 (3H, s), 3.39 (3H, s), 3.14 (1H, t, J= 8.5 Hz), 2.12 (1H, dd, J = 8.1, 5.1 Hz), 1.74 (1H, J = 9.0, 5.1 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.5, 166.4, 133.2, 133.0, 129.7, 128.2, 53.4, 52.8, 37.8, 32.4, IR (neat) cm , 1731, 1490, MS (CI) calcd for C1 3 H 13 ClO 4 : 268, found 269. Fe Dimethyl cyclopropane-1,1-dicarboxylateferrocene (Table 2). Solvent used for chromatography: 8:1 hexanes:ethyl acetate. Orange solid. 535 mg (62 %). 1H NMR (300 MHz, CDCl 3 ) δ 4.23 (1H, ddd, J = 2.5, 1.3, 1.3 Hz), 4.14 (5H, s), 4.07 (1H, ddd, J = 2.5, 2.5, 1.3 Hz), (1H, m), (1H, m), 3.72 (3H, s), 3.43 (3H, s), 2.88 (1H, dd, J = 9.3, 7.9 Hz), 1.82 (1H, dd, J = 7.9, 5.0 Hz), 1.70 (1H, dd, J = 9.3, 5.0 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.8, 167.0, 81.5, 69.2, 68.6, 68.3, 67.1, 65.9, 52.4, 52.0, 38.2, 29.2, IR (neat) cm , 3083, 2961, 1731, P5
7 MS (CI) calcd for C 17 H 18 F e O 4 : 342, found: 343. m.p. (from hexanes/ethyl acetate) ºC. MeO 2 C CO2 Me MeO Dimethyl 2-(4-methoxyphenyl) cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: Gradient from 9:1 to 6:1 hexanes: ethyl acetate. Colorless oil g (87 %). 1H NMR (300 MHz, CDCl 3 ) δ 7.10 (2H, d, J = 8.5 Hz), 6.79 (2H, d, J = 8.5 Hz), 3.74 (6H, s), 3.37 (3H, s), 3.17 (1H, t, J = 8.6 Hz), 2.14 (1H, dd, J = 8.0, 5.1 Hz), 1.72 (1H, dd, J= 9.3, 5.1 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.8, 166.7, 158.5, 129.5, 126.3, 55.6, 53.2, 52.7, 37.7, 32.8, IR (neat) cm , 2955, 2837, 1731, 1613, 1516, MS (CI) calcd for C 14 H 16 O 5 : 264, found: 265. MeO 2 C CO2 Me OMe Dimethyl 2-(2-methoxyphenyl)cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: 4:1 hexanes:ethyl acetate. Colorless oil. 576 mg (87 %). 1H NMR (300 MHz, CDCl 3 ) δ (1H, m), 6.99 (1H, dd, J = 7.5, 1.7 Hz), (2H, m), 3.82 (3H, s), 3.79 (3H, s), (1H, m), 3.33 (3H, s), 2.20 (1H, dd, J = 8.3, 5.1 Hz), 1.73 (1H, dd, J = 9.2, 5.1 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 170.4, 167.3, 159.1, 128.6, 127.8, 123.1, 119.9, 110.0, 55.5, 52.6, 52.0, 36.3, 28.5, IR (neat) cm , 2950, 1728, MS (CI) calcd for C 14 H 16 O 5 : 264, found: 265. P6
8 MeO 2 C CO2 Me NC Dimethyl-2-(4-cyanophenyl)cyclopropane-1,1-dicarboxylate (Table 2). 0.8 mol % of catalyst was used. Solvent used for chromatography: MTBE. White solid. 550 mg (44 %). 1H NMR (300 MHz, CDCl 3 ) δ 7.56 (2H, d, J = 8.0 Hz), 7.28 (2H, d, J = 8.0 Hz), 3.79 (3H, s), 3.39 (3H, s), 3.22 (1H, t, J = 7.0 Hz), 2.18 (1H, dd, J = 7.0, 4.0 Hz), 1.79 (1H, dd, J = 7.0, 4.0 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.6, 166.5, 140.3, 131.9, 129.2, 118.5, 111.3, 53.0, 52.5, 37.6, 31.8, IR (KBr) cm , 2966, 2234, 1718, MS (CI) calcd for C 14 H 13 NO 4 : 259, found: 260. m.p. (from MTBE] C. MeO 2 C MeO 2 C H 3 CO N O Dimethyl-2-(4-(5-methoxy-4-(methoxycarbonyl)oxazol-2-yl)phenyl)- cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: MTBE. White solid. 450 mg (24 %). 1H NMR (300 MHz, CDCl 3 ) δ 7.85 (2H, d, J = 8 Hz), 7.23 (2H, d, J = 8 Hz), 4.23 (3H, s), 3.88 (3H, s), 3.76 (3H, s), 3.34 (3H, s), 3.21 (1H, t, J = 7.0 Hz), 2.19 (1H, dd, J = 7.0, 4.0 Hz), 1.75 (1H, dd, J = 7.0, 4.0 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.8, 166.7, 161.8, 161.7, 150.1, 137.3, 128.8, 125.6, 125.3, 107.4, 59.8, 52.9, 52.3, 51.8, 37.4, 32.1, IR (KBr) cm , 2960, 1716, 1617, MS (CI) calcd for C 19 H 19 NO 8 : 389, found: 390. m.p. (from MTBE] C. P7
9 Br MeO 2 C Dimethyl 2-(3-bromophenyl)cyclopropane-1,1-dicarboxylate (Table 2). Solvent used for chromatography: 9:1 hexanes:ethyl acetate. Colorless oil. 640 mg (82 %). 1H NMR (300 MHz, CDCl 3 ) δ (2H, m), (2H, m), 3.81(3H, s), 3.44 (3H, s), 3.20 (1H, t, J = 8.5 Hz), 2.17 (1H, dd, J = 8.0, 5.4 Hz), 1.75 (1H, dd, J = 9.0, 5.4 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 170.1, 167.5, 134.2, 131.2, 130.4, 128.1, 126.8, 126.1, 52.8, 52.4, 39.0, 30.0, 27.7, 25.2, IR (neat) cm , 3952, 1728, 1566, MS (CI) calcd for C 13 H 13 BrO 4 : 312 found: 313. MeO 2 C CO2 Me Br Dimethyl 2-(2-bromophenyl)cyclopropane-1,1-dicarboxylate (Table 2). The experiment was run on a 3.5 mmol scale. Solvent used for chromatography: gradient from 12:1 to 6:1 hexanes:ethyl acetate. Colorless liquid. 857 mg (78 %). 1H NMR (300 MHz, CDCl 3 ) δ 7.52 (1H, dd, J = 7.8, 1.2 Hz), 7.21 (1H, ddd, J = 8.6, 7.5, 1.2 Hz ), (2H, m), 3.79 (3H, s), 3.34 (3H, s), (1H, m), 2.23 (1H, dd, J = 8.3, 2.3 Hz), 1.77 (1H, dd, J = 9.1, 5.2 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.7, 166.8, 134.3, 132.4, , , 126.9, 52.8, 52.1, 36.4, 33.7, IR (neat) cm , 2863, 1729, MS (CI) calcd for C 13 H 13 BrO 4 : 312, found: 313. MeO 2 C Dimethyl 2-hexylcyclopropane-1,1-dicarboxylate (Table 3). The experiment was run in a 5 mmol scale. Solvent used for chromatography: 15:1 hexanes:ethyl acetate. Colorless oil. 1.1 g (91 %). 1H NMR (300 MHz, CDCl 3 ) δ 3.71 (3H, s), 3.68 (3H, s), (1H, m), (12H, m), 0.84 (3H, t, J = 6.8 Hz). P8
10 13C NMR (75 MHz, CDCl 3 ) δ 170.9, 168.6, 52.4, 52.3, 33.8, 31.6, 28.8, 28.7, 28.7, 28.6, 22.5, 21.3, IR (neat) cm , 2929, 2858, 1725, MS (CI) calcd for C 13 H 22 O 4 : 242 found: 243. O MeO 2 C Dimethyl 2-(butoxymethyl)cyclopropane-1,1-dicarboxylate (Table 3). Solvent used for chromatography: 15:1 hexanes:ethyl acetate. Colorless liquid. 531 mg (87 %). 1H NMR (300 MHz, CDCl 3 ) δ 3.70 (3H, s), 3.67 (3H, s), (4H, m), (1H, m), (6H, m), 0.85 (3H, t, J = 7.3 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 170.3, 168.1, 70.6, 68.1, 52.5, 52.4, 32.5, 31.5, 27.3, 19.1, 18.8, IR (neat) cm , 2935, 2871, 1731, MS (CI) calcd for C 12 H 20 O 5 : 244, found: 245. O MeO 2 C CO2 Me Dimethyl 2-(phenoxymethyl)cyclopropane-1,1-dicarboxylate (Table 3). Solvent used for chromatography: 5:1 hexanes:ethyl acetate. Colorless oil. 473 mg (72 %). 1H NMR (300 MHz, CDCl 3 ) δ (2H, m), 6.92 (1H, tt, J = 7.5, 1.0 Hz), (2H, m), 4.11 (1H, dd, J = 10.4, 5.3 Hz), 3.93 (1H, dd, J = 10.4, 7.2 Hz), 3.73 (3H, s), 3.64 (3H, s), (1H, m), 1.70 (1H, dd, J = 7.6, 4.9 Hz), 1.52 (1H, dd, J = 9.2, 4.9 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 169.9, 167.9, 158.2, 129.2, 120.9, 114.3, 65.3, 52.5, 52.5, 32.6, 26.5, IR (neat) cm , 2956, 1731, MS (CI) calcd for C 14 H 16 O 5 : 264, found: 265. O MeO 2 C Dimethyl 2-(benzyloxymethyl)cyclopropane-1,1-dicarboxylate (Table 3). The experiment was run in a 3.5 mmol scale. Solvent used for chromatography: gradient from 15:1 to 7:1 hexanes:ethyl acetate. Colorless oil. 808 mg (82 %). P9
11 1H NMR (300 MHz, CDCl 3 ) δ (5H, m), 4.48 (2H, d, J = 4.0 Hz), 3.74 (3H, s), 3.70 (3H, s), 3.60 (1H, dd, J = 10.5, 5.7 Hz), 3.47 (1H, dd, J = 10.5, 7.1 Hz), (1H, m), 1.60 (1H, dd, J = 7.5, 4.7 Hz), 1.48 (1H, dd, J = 9.34, 4.7 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 170.3, 168.1, 137.8, 128.3, 127.6, 127.5, 72.8, 67.7, 52.6, 52.2, 32.6, 27.3, IR (neat) cm , 2952, 1727, 1477, MS (CI) calcd for C 15 H 18 O 5 : 278, found: 279. MeO 2 C CO2 Me Dimethyl 2-phenethylcyclopropane-1,1-dicarboxylate (Table 3). Solvent used for chromatography: 9:1 hexanes:ethyl acetate. Colorless liquid. 620 mg (95 %). 1H NMR (300 MHz, CDCl 3 ) δ (2H, m), (3H, m), 3.78 (3H, s), 3.74 (3H, s), 2.75 (2H, ddd, J = 9.4, 6.6, 2.4 Hz), (1H, m), (1H, m), (1H, m), (2H, m). 13C NMR (75 MHz, CDCl 3 ) δ 170.7, 168.6, 141.2, 128.3, 125.9, 52.5, 52.4, 35.0, 33.9, 30.7, 28.1, IR (neat) cm , 1722, 1436, MS (CI) calcd for C 15 H 18 O 4 : 262, found: 263. MeO 2 C Dimethyl 2-(2-methylpentan-2-yl)cyclopropane-1,1-dicarboxylate (Table 3). Solvent used for chromatography: 15:1 hexanes:ethyl acetate. Colorless oil. 550 mg (91 %). 1H NMR (300 MHz, CDCl 3 ) δ 3.71 (3H, s), 3.68 (3H, s), 1.84 (1H, t, J = 9.0 Hz), 1.47 (1H, dd, J = 9.0, 4.8 Hz), (5H, m), (6H, m), 0.72 (3H, s). 13C NMR (75 MHz, CDCl 3 ) δ 171.6, 169.0, 52.6, 52.3, 46.2, 39.1, 33.0, 32.7, 25.2, 24.3, 17.2, 17.2, IR (neat) cm , 2873, 1731, MS (CI) calcd for C 13 H 22 O 4 : 242, found: 243. P10
12 H H Dimethyl bicyclo[5.1.0]octane-8,8-dicarboxylate (Table 3). Solvent used for chromatography: 8:1 hexane:etoac. Colorless oil. 407 mg (72 %). 1H NMR (300 MHz, CDCl 3 ) δ 3.76 (3H, s), 3.70 (3H, s), (2H, m), (5H, m), (2H, m), (3H, m) 13C NMR (75 MHz, CDCl 3 ) δ 170.8, 167.7, 52.4, 52.0, 40.7, 31.9, 31.8, 28.2, IR (neat) cm , 2924, 2850, 1728, MS (CI) calcd for C 12 H 18 O 4 : 226, found: 227. MeO 2 C H Dimethyl 2,3-dihydro-1H-cyclopropa[a]naphthalene-1,1(1aH,7bH)- dicarboxylate (Table 3). 0.5 mol % of catalyst was used. Reaction time: 14 hours. Solvent used for chromatography: 15:1 hexanes:ethyl acetate. White solid. 530 mg (82 %). 1H NMR (300 MHz, CDCl 3 ) δ (1H, m), (2H, m), (1H, m), 3.74 (3H, s), 3.51 (3H, s), 2.82 (1H, d, J = 9.2 Hz), (1H, m), (4H, m). 13C NMR (75 MHz, CDCl 3 ) δ 170.1, 167.5, 134.2, 131.2, 130.4, 128.1, 126.8, 126.1, 52.8, 52.4, 39.0, 30.0, 27.7, 25.2, IR (neat) cm , 1751, 1449, MS (CI) calcd for C 15 H 16 O 4 : 260 found: 261. m.p. (from hexanes/ethyl acetate) ºC. H H H Cycloprop[a]indene-1,1(1aH)-dicarboxylic acid, 6,6a-dihydro-dimethyl ester (Table 3). Solvent used for chromatography: 9:1 hexanes:ethyl acetate. Colorless oil. 555 mg (89 %). 1H NMR (300 MHz, CDCl 3 ) δ (1H, m), (3H, m), 3.73 (3H, s), (3H, m), 3.22 (3H, s), (1H, m). P11
13 13C NMR (75 MHz, CDCl 3 ) δ 169.8, 166.0, 141.5, 140.1, 127.1, 125.4, 124.8, 52.8, 51.9, 39.4, 33.5, IR (neat) cm , 2952, 2843, 1716, MS (CI) calcd for C 14 H 14 O 4 : 246, found: 247. MeO 2 C H H Me Cis-(2S*,3S*)-Dimethyl 2-methyl-3-phenylcyclopropane-1,1-dicarboxylate (Table 3). 0.5 mol % of catalyst was used. Reaction time: 14 hours. Solvent used for chromatography: 9:1 hexanes:ethyl acetate. Colorless oil mg (87 %). 1H NMR (300 MHz, CDCl 3 ) δ (5H, m), 3.69 (3H, s), 3.53 (3H, s), 3.01 (1H, d, J = 9.9 Hz), (1H, m), 1.24 (3H, d, J = 6.8 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 177.2, 167.2, 133.5, 130.0, 127.9, 126.8, 52.8, 51.9, 37.6, 34.8, 27.0, IR (neat) cm , 1728, 1603, 1499, MS (CI) calcd for C 14 H 16 O 4 : 248, found: 249. The relative stereochemistry was established by ROESY. MeO 2 C H CO2 Me Me H Trans-(2R*,3S*)-dimethyl 2-methyl-3-phenylcyclopropane-1,1- dicarboxylate (Table 3). 1 mol % of catalyst was used. Solvent used for chromatography: 8:1 hexane:etoac. Colorless oil. 174 mg (28 %). 1H NMR (300 MHz, CDCl 3 ) δ (5H, m), 3.79 (3H, s), 3.37 (3H, s), 3.06 (1H, d, J = 8.1 Hz), 2.56 (1H, dq, J = 8.1, 6.4 Hz), 1.27 (3H, d, J = 6.4 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 168.3, 167.4, 135.0, 128.4, 128.0, 127.0, 52.5, 52.1, 43.1, 37.8, 25.1, IR (neat) cm , 2945, 1731, MS (CI) calcd for C 14 H 16 O 4 : 248, found: 249. The relative stereochemistry was established by NOESY. 3 This compound has been recently reported to be a solid of low melting point : A. Karadeolian, M. A. Kerr, J. Org. Chem. 2007, 72, P12
14 MeO 2 C H H Cl Cl (2R*,3S*)-dimethyl 2-chloro-3-(chloromethyl)cyclopropane-1,1- dicarboxylate (Table 3). Solvent used for chromatography: Gradient from 7:3 to 7:4 cyclohexane:1,2-dichloroethane. Colorless oil. 263 mg (43 %). 1H NMR (300 MHz, CDCl 3 ) δ 4.03 (1H, dd, J = 11.9, 4.5 Hz), 3.88 (1H, d, J = 7.7 Hz), 3.78 (3H, s), 3.74 (3H, s), 3.64 (1H, dd, J = 11.9, 10.2 Hz), 2.25 (1H, ddd, J = 10.2, 7.6, 4.6 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 167.8, 164.0, 53.4, 53.4, 39.9, 39.4, 39.3, IR (neat) cm , 1731, MS (CI) calcd for C 8 H 10 Cl 2 O 4 : 240, found: 241. The relative stereochemistry was established by ROESY. MeO 2 C H H (2R*,3S*)-dimethyl 2,3-dipropylcyclopropane-1,1-dicarboxylate (Table 3). Solvent used for chromatography: Gradient from 7:3 to 7:4 cyclohexane:1,2- dichloroethane. Colorless oil. 246 mg (41%). 1H NMR (300 MHz, CDCl 3 ) δ 3.71 (3H, s), 3.68 (3H, s), (10H, m), 0.92 (6H, t, J = 7.1 Hz). 13C NMR (75 MHz, CDCl 3 ) δ 171.6, 167.7, 52.4, 51.8, 36.1, 31.4, 26.5, 22.4, IR (neat) cm , 2934, 2873, 1728, MS (CI) calcd for C 13 H 22 O 4 : 242, found: 243. MeO 2 C Dimethyl 2-ethyl-3-(E)-heptene-1,1-dicarboxylate (Table 3). Solvent used for chromatography: Gradient from 7:3 to 7:4 cyclohexane:1,2-dichloroethane. Colorless oil. 470 mg. The compound was isolated as a mixture. The minor component could not be separated by standard techniques, but GC-MS data suggests that it is a positional isomer. Spectroscopic data for the trans isomer: 1H NMR (300 MHz, CDCl 3 ) δ 5.44 (1H, dt, J = 15.1, 7.0 Hz), 5.13 (1H, ddt, J = 15.3, 9.4, 1.2 Hz), 3.67 (3H, s), 3.62 (3H, s), 3.30 (1H, d, J = 9.2 Hz), 2.57 (1H, P13
15 ddd, J = 19.0, 9.5, 3.7 Hz), 1.91 (2H, m), (4H, m), 0.82 (3H, t, J = 7.3), 0.81 (3H, t, J = 7.3). 13C NMR (75 MHz, CDCl 3 ) δ 168.8, 168.5, 133.8, 129.1, 57.0, 52.1, 51.9, 44.9, 34.4, 25.6, 22.4, 13.3, IR (neat) cm , 2932,l 2875, 1739, MS (CI) calcd for C 13 H 22 O 4 : 242, found: 243. NC MeO 2 C Dimethyl-2-(cyanomethyl)cyclopropane-1,1-dicarboxylate (Scheme 2). 0.7 mol % of catalyst was used. Solvent used for chromatography: MTBE. Colorless oil. 420 mg (39 %). 1H NMR (300 MHz, CDCl 3 ) δ 3.80 (3H, s), 3.74 (3H, s), 2.55 (2H, d, J = 7.0 Hz), (1H, m), (2H, m). 13C NMR (75 MHz, CDCl 3 ) δ 169.1, 167.7, 117.2, 53.1, 53.0, 33.2, 22.5, 20.5, IR (neat) cm , 2958, 2254, 1735, MS (CI) calcd for C 9 H 11 NO 4 : 197, found: 198. MeO 2 C N O OMe Dimethyl 2-((4-methoxy-5-(methoxycarbonyl)oxazol-2- yl)methyl)cyclopropane-1,1-dicarboxylate (Scheme 2). 0.7 mol % of catalyst was used. Solvent used for chromatography: MTBE. White solid. 400 mg (23 %). 1H NMR (300 MHz, CDCl 3 ) δ 4.10 (3H, s), 3.81 (3H, s), 3.72 (3H, s), 3.68 (3H, s), 2.88 (1H, dd, J = 7.0 Hz, 3.0 Hz), 2.65 (1H, dd, J = 6.0 Hz, 3.0 Hz), (1H, m), (2H, m). 13C NMR (75 MHz, CDCl 3 ) δ 169.6, 168.0, 161.7, 161.6, 151.3, 105.9, 59.7, 52.7, 52.7, 51.6, 33.3, 27.2, 24.5, IR (KBr) cm , 2957, 2873, 1720, 1639, 1206, MS (CI) calcd for C 14 H 17 NO 8 : 327, found: 328. m.p. (from MTBE] 108 C. P14
16 MeO 2 C CN Dimethyl-2-(3-cyanopropyl)cyclopropane-1,1-dicarboxylate (Scheme 2). 1.8 mol % of catalyst was used. Solvent used for chromatography: MTBE. Colorless oil. 510 mg (52 %). 1H NMR (300 MHz, CDCl 3 ) δ 3.76 (3H, s), 3.71 (3H, s), 2.36 (2H, t, J = 7.0 Hz), (3H, m), (1H, m), (3H, m). 13C NMR (75 MHz, CDCl 3 ) δ 170.4, 168.3, 119.2, 52.7, 52.7, 33.7, 27.5, 27.1, 24.7, 20.8, IR (neat) cm , 2245, 1736, 1439, 1216, MS (CI) calcd for C 11 H 15 NO 4 : 225, found: 226. MeO 2 C N O OCH 3 Methyl 2-(3-(2-acetoxy-2-(methoxycarbonyl)cyclopropyl)propyl)-5- methoxyoxazole-4-carboxylate (Scheme 2). 1.8 mol % of catalyst was used. Solvent used for chromatography: MTBE. Colorless oil. 270 mg (17 %). 1H NMR (300 MHz, CDCl 3 ) δ 4.10 (3H, s), 3.80 (3H, s), 3.68 (3H, s), 3.65 (3H, s), 2.64 (2H, t, J = 7.0 Hz), (3H, m), (1H, m), (3H, m). 13C NMR (75 MHz, CDCl 3 ) δ 170.4, 168.3, 161.7, 161.6, 153.3, 105.6, 59.6, 52.5, 52.4, 51.5, 33.7, 27.8, 27.7, 27.5, 25.7, IR (neat) cm , 2955, 1732, MS (CI) calcd for C 16 H 21 NO 8 : 355, found: 356. MeO 2 C Me Dimethyl 2-methyl-3-phenyl-2-cyclopropene-1,1-dicarboxylate (Scheme 3). 1 mol % of catalyst was used. The reaction was run in 25 mmol scale. Reaction time: 14 hours. Solvent used for chromatography: 6:1 hexane:etoac. White solid 4.35 g (71%). 1H NMR (300 MHz, CDCl 3 ) δ (5H, m), 3.68 (6H, s), 2.33 (3H, s). P15
17 13C NMR (75 MHz, CDCl 3 ) δ 171.3, 129.5, 129.3, 128.7, 124.9, 105.1, 104.7, 52.0, 34.9, 9.4. IR (neat) cm , 2952, 1747, 1710, MS (CI) calcd for C 14 H 14 O 4 : 246, found: 247. m.p. (from cyclohexane/mtbe) C. P16
18 MeO 2 C Chloroform-d
19 MeO 2 C Chloroform-d
20 Chloroform-d 7.24 MeO 2 C F
21 8/9/2007 1:58 PM MeO 2 C F Chloroform-d
22 MeO F 2 C F Chloroform-d
23 F MeO 2 C F Chloroform-d
24 Chloroform-d 7.24 MeO 2 C F 3 C
25 MeO 2 C F 3 C Chloroform-d
26 EtO 2 C CO2 Et F Chloroform-d
27 EtO 2 C CO2 Et F Chloroform-d
28 F MeO F 2 C F F F Chloroform-d
29 Chloroform-d MeO F 2 C F F F F
30 MeO 2 C Cl Chloroform-d
31 Chloroform-d MeO 2 C Cl
32 Fe
33 Fe
34 MeO 2 C MeO Chloroform-d
35 Chloroform-d MeO 2 C MeO
36 MeO 2 C OMe
37 MeO 2 C OMe
38 N H 3 COOC COOCH 3 Chloroform-d Water
39 Chloroform-d N H 3 COOC COOCH
40 Chloroform-d H 3 COOC COOCH 3 N H 3 COOC O H 3 CO
41 Chloroform-d H 3 COOC COOCH 3 N H 3 COOC O H 3 CO
42 Br MeO 2 C Chloroform-d
43 Br MeO 2 C Chloroform-d
44 MeO 2 C CO2 Me Br
45 MeO 2 C CO2 Me Br Chloroform-d
46 MeO 2 C Chloroform-d
47 MeO 2 C Chloroform-d
48 O MeO 2 C Chloroform-d
49 O MeO 2 C Chloroform-d
50 O
51 O
52 O MeO 2 C
53 O MeO 2 C Chloroform-d
54 MeO 2 C CO2 Me
55 MeO 2 C Chloroform-d
56 MeO 2 C Chloroform-d
57 Chloroform-d MeO 2 C
58
59
60 H CO 2Me H Chloroform-d
61 MeO 2 C CDCl
62 H H Chloroform-d
63 H H CDCl
64 MeO 2 C H H
65 MeO 2 C H H Chloroform-d
66 MeO 2 C H CO2 Me Me H
67 MeO 2 C H CO2 Me Me H
68 MeO 2 C H Cl H Cl Chloroform-d
69 MeO 2 C H Cl H Cl Chloroform-d
70 MeO 2 C H H
71 MeO 2 C H H
72 MeO 2 C
73 MeO 2 C Chloroform-d
74 H 3 COOC COOCH 3 N Chloroform-d
75 Chloroform-d H 3 COOC COOCH 3 N
76 Chloroform-d MeOOC COOMe O N MeO COOMe
77 Chloroform-d MeOOC COOMe O N MeO COOMe
78 H 3 COOC COOCH 3 N Chloroform-d Water MTBE
79 H 3 COOC COOCH 3 N
80 Chloroform-d H 3 COOC H 3 CO N COOCH O 3 H 3 COOC
81 Chloroform-d H 3 COOC H 3 CO N COOCH O 3 H 3 COOC
82 MeO 2 C Me
83 Chloroform-d MeO 2 C Me
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