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1 Supporting Information Wiley-VCH Weinheim, Germany
2 Synthesis of Homoallylic Sulfones Using a Novel Decarboxylative Claisen Rearrangement Reaction** Damien Bourgeois, Donald Craig,* N. Paul King, and David M. Mountford Spectroscopic and physical data for compounds 2a-2n (±)-1-Methyl-4-(2-propyl-but-3-ene-1-sulfonyl)-benzene 2a R F 0.19 (10% ethyl acetate petrol); ν max (film) 2961, 2929, 2874, 1642, 1598, 1464, 1403, 1313 (SO 2 ), 1301, 1148 (SO 2 ), 1088, 992, 917 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.74 (2H, d, J = 8.4 Hz, ortho SO 2 -Ar-CH 3 ), 7.30 (2H, d, J = 8.4 Hz, meta SO 2 -Ar-CH 3 ), (1H, m, H-3), (2H, m, CH 2-4), 3.07 (2H, d, J = 6.2 Hz, CH 2-1), (1H, m, H-2), 2.41 (3H, s, SO 2 -Ar-CH 3 ), (4H, m, CH 2-3', CH 2-4'), 0.81 (3H, t, J = 7.2 Hz, CH 3-5'); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar-CH 3 ), (C-3), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 -Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-4), 61.0 (C-1), 38.4 (C-3'), 36.6 (C-2), 21.6 (SO 2 -Ar-CH 3 ), 19.7 (C-4'), 13.8 (C-5'); m/z (CI) 270 [MNH 4 ] +, 253 [MH] +, 96 (Found: C 14 H 20 O 2 S requires ) (Found: C, 66.70; H, C 26 H 36 N 2 O 3 S requires C, 66.63; H, 7.99). [*] Dr. D. Bourgeois, Prof. Dr. D. Craig, D. M. Mountford Department of Chemistry Imperial College London South Kensington Campus London SW7 2AZ (U.K.) Fax: (+44) d.craig@imperial.ac.uk Dr. N. Paul King Neurology and GI Centre of Excellence for Drug Discovery GlaxoSmithKline Research Limited New Frontiers Science Park Third Avenue Harlow Essex CM19 5AW (U.K.) [**] We thank EPSRC (grant GR/N31412: postdoctoral research associateship to D. B.) and EPSRC/GlaxoSmithKline (supported DTA studentship to D. M. M.) for financial support of this research. 1
3 (±)-trans-1-methyl-4-(2-vinyl-pent-3-ene-1-sulfonyl)benzene 2c R F 0.23 (20% ethyl acetate petrol); ν max (film) 3030, 2967, 2919, 2884, 1638, 1598, 1450, 1403, 1319 (SO 2 ), 1308, 1146 (SO 2 ), 1087, 968 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.72 (2H, d, J = 8.2 Hz, ortho SO 2 -Ar-CH 3 ), 7.30 (2H, d, J = 8.0 Hz, meta SO 2 -Ar-CH 3 ), (1H, m, H-3'), (1H, m, H-3), (1H, m, H-4), (2H, m, CH 2-4'), (1H, s, H-2), (2H, m, CH 2-1), 2.40 (3H, s, SO 2 -Ar-CH 3 ), 1.18 (3H, d, J = 7.2 Hz, CH 3-5); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar-CH 3 ), (C-3'), (ipso SO 2 -Ar- CH 3 ), (C-3), (meta SO 2 -Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-4), (C-4'), 59.7 (C-1), 40.7 (C-2), 20.9 (SO 2 -Ar-CH 3 ), 17.2 (C-5); m/z (CI) 268 [MNH 4 ] +, 251 [MH] +, 174, 139, 94 (Found: [MH] +, C 14 H 18 O 2 S requires [MH] +, ) (Found: C, 67.06; H, C 14 H 18 O 2 S requires C, 67.16; H, 7.25). (±)-(2-(p-Toluenesulfonylmethyl)-but-3-enyloxymethyl)-benzene 2d BnO R F 0.19 (20% ethyl acetate petrol); ν max (film) 3031, 2924, 2862, 1597, 1495, 1454, 1401, 1361, 1313 (SO 2 ), 1302, 1146 (SO 2 ), 1088, 914, 818, 735, 700, 663 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.75 (2H, d, J = 8.4 Hz, ortho SO 2 -Ar-CH 3 ), (7H, m, meta SO 2 -Ar-CH 3, Ph), (1H, m, H-3), (2H, m, CH 2-4), 4.42 (2H, d, J = 1.7 Hz, CH 2 -Ph), (3H, m, H-1, CH 2 -SO 2 -Ar-CH 3 ), 3.12 (1H, dd, J = 14.2, 7.5 Hz, H-1), (1H, m, H-2), 2.42 (3H, s, SO 2 -Ar-CH 3 ); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar-CH 3 ), (ipso Ph), (ipso SO 2 -Ar-CH 3 ), (C-3), (meta SO 2 -Ar-CH 3 ), (meta Ph), (ortho Ph), (para Ph), (ortho SO 2 -Ar-CH 3 ), (C-2), 73.1 (CH 2 -Ph), 72.0 (C-1), 57.5 (CH 2 -SO 2 -Ar-CH 3 ), 39.0 (C-2), 21.7 (SO 2 -Ar-CH 3 ); m/z (CI) 348 [MNH 4 ] +, 331 [MH] +, 139, 108, 91 (Found: [MH] +, C 19 H 23 SO 3 requires [MH] +, ). (±)-1-(2-Phenylbut-3-ene-1-sulfonyl)-4-methyl-benzene 2e Ph R F 0.21 (20% ethyl acetate petrol); mp C; ν max (film) 3062, 3030, 2924, 1637, 1599, 1493, 1454, 1402, 1319 (SO 2 ), 1290, 1142 (SO 2 ), 1088, 918, 818, 748, 702, 667 cm -1 ; δ H 2
4 (270 MHz, CDCl 3 ) 7.63 (2H, d, J = 6.9 Hz, ortho SO 2 -Ar-CH 3 ), (7H, m, meta SO 2 -Ar-CH 3, Ph), (1H, m, H-3), (2H, m, CH 2-4), (1H, m, H- 2), (2H, m, CH 2-1), 2.38 (3H, s, SO 2 -Ar-CH 3 ); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar-CH 3 ), (ipso Ph), (C-3), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 -Ar- CH 3 ), (meta Ph), (ortho Ph), (ortho SO 2 -Ar-CH 3 ), (para Ph), (C-4), 61.1 (C-1), 44.4 (C-2), 21.6 (SO 2 -Ar-CH 3 ); m/z (CI) 304 [MNH 4 ] +, 287 [MH] +, 176, 130 (Found: [MNH 4 ] +, C 17 H 18 SO 2 requires [MNH 4 ] +, ). (±)-1-(2-Phenyl-3-methyl-but-3-ene-1-sulfonyl)-4-methylbenzene 2f Ph R F 0.24 (20% ethyl acetate petrol); mp C; ν max (film) 3055, 2985, 1647, 1599, 1493, 1452, 1421, 1315, 1302, 1265 (SO 2 ), 1155 (SO 2 ), 1136, 1088, 897, 746, 706, 663 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.58 (2H, d, J = 8.2 Hz, ortho SO 2 -Ar-CH 3 ), (7H, m, meta SO 2 -Ar-CH 3, Ph), 4.82 (2H, d, J = 9.2 Hz, CH 2-4), 3.85 (1H, t, J = 6.9 Hz, H-2), (2H, m, CH 2-1), 2.35 (3H, s, SO 2 -Ar-CH 3 ), 1.55 (3H, s, CH 3-4'); δ C (67.5 MHz, CDCl 3 ) (C-3), (para SO 2 -Ar-CH 3 ), (ipso Ph), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 -Ar-CH 3 ), (meta Ph), (ortho Ph), (ortho SO 2 -Ar-CH 3 ), (para Ph), (C-4), 59.6 (C-1), 47.3 (C-2), 21.6 (SO 2 -Ar-CH 3 ), 21.0 (C-4'); m/z (CI) 318 [MNH 4 ] +, 301 [MH] +, 144 (Found: [MNH 4 ] +, C 18 H 20 SO 2 requires [MNH 4 ] +, ) (Found: C, 71.69; H, C 18 H 20 SO 2 requires C, 71.96; H, 6.71). 1-(2,2-Dimethyl-but-3-ene-1-sulfonyl)-4-methyl-benzene 2g ν max (film) 2988, 2876, 2857, 1641, 1315 (SO 2 ), 1182 (SO 2 ), 817, 700 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.70 (2H, d, J = 8.0 Hz, ortho SO 2 -Ar-CH 3 ), 7.26 (2H, d, J = 8.0 Hz, meta SO 2 -Ar- CH 3 ), 5.82 (1H, dd, J = 17.5, 10.5 Hz, H-2), 4.92 (1H, dd, J = 17.5, 1.0 Hz, H-1), 4.87 (1H, dd, J = 10.5, 1.0 Hz, H-1), 3.06 (2H, s, CH 2 -SO 2 -Ar-CH 3 ), 2.34 (3H, s, SO 2 -Ar-CH 3 ), 1.20 (3H, s, 2 CH 3-4); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar-CH 3 ), (C-2), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 -Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-1), 66.8 (CH 2 -SO 2 -Ar-CH 3 ), 37.4 (2 C-4), 26.9 (C-3), 21.6 (SO 2 -Ar-CH 3 ); m/z (CI) 256 [MNH 4 ] +, 239 [MH] +, 174, 139 (Found: [MNH 4 ] +, C 13 H 18 SO 2 requires [MNH 4 ] +, ). 3
5 (±)-1-(2,6-Dimethyl-2-vinyl-hept-5-ene-1-sulfonyl)-4-methyl-benzene 2h R F 0.20 (10% ethyl acetate petrol); ν max (film) 2968, 2922, 2858, 1637, 1599, 1452, 1402, 1379, 1317 (SO 2 ), 1147 (SO 2 ), 1088, 1001, 918, 818, 768, 660 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.72 (2H, d, J = 8.4 Hz, ortho SO 2 -Ar-CH 3 ), 7.28 (2H, d, J = 8.2 Hz, meta SO 2 -Ar-CH 3 ), 5.75 (1H, dd, J = 17.3, 10.9 Hz, H-3'), (2H, m, CH 2-4'), 3.09 (2H, s, CH 2 -SO 2 -Ar- CH 3 ), 2.38 (3H, s, SO 2 -Ar-CH 3 ), (2H, m, CH 2-4), (2H, m, CH 2-3), 1.61 (3H, d, J = 0.7 Hz, CH 3-7'), 1.52 (3H, s, CH 3-7), 1.25 (3H, m, CH 3-3''); δ C (67.5 MHz, CDCl 3 ) (C-3'), (para SO 2 -Ar-CH 3 ), (ipso SO 2 -Ar-CH 3 ), (C-6), (meta SO 2 -Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-5), (C-4'), 65.5 (C-1), 40.6 (C-3), 25.7 (C-7), 22.8 (C-2), 22.7(C-3''), 21.6 (SO 2 -Ar-CH 3 ), 21.1 (C-4), 17.7 (C-7'); m/z (CI) 324 [MNH 4 ] +, 151, 95 (Found: [MH] +, C 18 H 26 SO 2 requires [MH] +, ) (Found: C, 70.40; H, C 18 H 26 SO 2 requires C, 70.54; H, 8.55). (1R,4S)-1-(5-Isopropenyl-2-methylene-cyclohexylmethanesulfonyl)-4-methyl-benzene 2i R F 0.33 (20% ethyl acetate petrol); mp C; [α] D (c 0.93, CHCl 3 ); ν max (film) 2930, 2860, 1645, 1597, 1445, 1301 (SO 2 ), 1288, 1147 (SO 2 ), 1086, 896, 819, 757, 662, 591cm -1 ; δ H (270 MHz, CDCl 3 ) 7.75 (2H, d, J = 8.4 Hz, ortho SO 2 -Ar- CH 3 ), 7.30 (2H, d, J = 8.2 Hz, meta SO 2 -Ar-CH 3 ), (4H, m, CH 2-3', CH 2-7'), (2H, m, CH 2 -SO 2 -Ar-CH 3 ), (1H, m, H-1), 2.40 (3H, s, SO 2 -Ar-CH 3 ), (7H, m, H-5, CH 2-3, CH 2-4, CH 2-6), 1.63 (3H, s, CH 3-7''); δ C (67.5 MHz, CDCl 3 ) (C-2), (C-6'), (para SO 2 -Ar-CH 3 ), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 - Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-7'), (C-3'), 58.7 (CH 2 -SO 2 -Ar-CH 3 ), 39.2 (C-5), 37.8 (C-3), 36.5 (C-6), 32.7(C-1), 31.1 (C-4), 21.7 (SO 2 -Ar-CH 3 ), 21.0 (C-7''); m/z (CI) 626 [2MNH 4 ] +, 322 [MNH 4 ] +, 149, 52 (Found: [MNH 4 ] +, C 18 H 24 SO 2 requires [MNH 4 ] +, ) (Found: C, 71.07; H, C 18 H 24 SO 2 requires C, 71.01; H, 7.95%). 4
6 (1R,5R)-6,6-Dimethyl-2-methylene-3-(p-toluenesulfonylmethyl)bicyclo[3.1.1]heptane 2j 24 R F 0.32 (20% ethyl acetate petrol); mp C; [α] D (c 1.09, CHCl 3 ); ν max (film) 2976, 2922, 2871, 1637, 1597, 1458, 1404, 1302 (SO 2 ), 1171, 1147 (SO 2 ), 1088, 889, 815, 752, 660, 617 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.78 (2H, d, J = 8.2 Hz, ortho SO 2 -Ar-CH 3 ), 7.33 (2H, d, J = 8.1 Hz, meta SO 2 -Ar-CH 3 ), 4.65 (1H, s, H-1), 4.57 (1H, s, H- 1), 3.31(1H, s, CH 2 -SO 2 -Ar-CH 3 ), 3.28 (1H, d, J = 2.5 Hz, CH 2 -SO 2 -Ar-CH 3 ), (1H, m, H-3), 2.41 (3H, s, SO 2 -Ar-CH 3 ), (2H, m, H-5, H-7), (3H, m, H- 4 eq, CH 2-8), 1.17 (3H, s, CH 3-7'), 1.04 (1H, d, J = 10.1 Hz, H-4 ax ), 0.67 (3H, s, CH 3-7''); δ C (67.5 MHz, CDCl 3 ) (C-2), (para SO 2 -Ar-CH 3 ), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 -Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-3), 69.0 (CH 2 -SO 2 -Ar-CH 3 ), 51.8 (C-7), 40.7 (C-5), 40.0 (C-6), 31.2 (C-4), 29.4 (C-3), 28.6 (C-8), 25.7 (C-7'), 21.7 (SO 2 -Ar- CH 3 ), 21.6 (C-7''); m/z (CI) 322 [MNH 4 ] +, 305 [MH] +, 149 (Found: [MNH 4 ] +, C 18 H 24 SO 2 requires [MNH 4 ] +, ) (Found: C, 70.80; H, C 18 H 24 SO 2 requires C, 71.01; H, 7.95). (±)-1-Methyl-4-(1-methylcyclohex-2-enylmethanesulfonyl)benzene 2k R F 0.29 (20% ethyl acetate petrol); ν max (film) 2929, 2871, 2837, 1597, 1454, 1436, 1315 (SO 2 ), 1304, 1288, 1146 (SO 2 ), 1088, 818, 764, 733 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.74 (2H, d, J = 8.4 Hz, ortho SO 2 -Ar-CH 3 ), 7.28 (2H, d, J = 7.9 Hz, meta SO 2 -Ar- CH 3 ), (2H, m, H-2, H-3), 3.05 (2H, s, CH 2 -SO 2 -Ar-CH 3 ), 2.39 (3H, s, SO 2 -Ar- CH 3 ), (6H, m, CH 2-4, CH 2-5, CH 2-6), 1.25 (3H, s, CH 3-2'); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar-CH 3 ), (ipso SO 2 -Ar-CH 3 ), (C-2), (meta SO 2 -Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-3), 66.3 (CH 2 -SO 2 -Ar-CH 3 ), 35.8 (C-1), 35.0 (C-6), 27.3 (C-4), 24.7 (C-5), 21.6 (SO 2 -Ar-CH 3 ), 18.7 (C-2'); m/z (CI) 546 [2MNH 4 ] +, 282 [MNH 4 ] +, 265 [MH] +, 156, 109, 73, 61 (Found: [MH] +, C 15 H 20 SO 2 requires [MH] +, ). 5
7 (±)-((1,1-Dimethyl)ethyl[1-isobutyl-2-(p-toluenesulfonylmethyl)but-3-enyloxy-dimethylsilane 2l OTBS ν max (film) 2964, 2857, 1469, 1340 (SO 2 ), 1047 (SO 2 ), 893, 776, 664 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.72 (2H, d, J = 8.0 Hz, ortho SO 2 -Ar-CH 3 ), 7.32 (2H, d, J = 8.0 Hz, meta SO 2 -Ar- CH 3 ), 5.61 (1H, ddd, J = 19.0, 10.5, 8.5 Hz, H-2), (2H, m, CH 2-1), 3.87 (1H, ddd, J = 9.0, 6.0, 3.0 Hz, H-4), 3.40 (1H, dd, J = 14.0, 4.0, CH 2 -SO 2 -Ar-CH 3 ), 3.04 (1H, dd, J = 14.0, 5.5, CH 2 -SO 2 -Ar-CH 3 ), (1H, m, H-3), 2.41 (3H, s, SO 2 -Ar-CH 3 ), 1.55 (1H, sept, J = 7.0 Hz, H-6), (2H, m, CH 2-5), 0.87 (3H, d, J = 7.0 Hz, CH 3-7), 0.82 (9H, s, Si-tBu), 0.80 (3H, d, J = 7.0 Hz, CH 3-7'), 0.01 (3H, s, Si-Me), 0.00(3H, s, Si-Me); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar-CH 3 ), (C-2), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 -Ar-CH 3 ), (ortho SO 2 -Ar-CH 3 ), (C-1), 72.6 (C-4), 56.9 (CH 2 -SO 2 -Ar- CH 3 ), 44.1 (C-5), 42.6 (C-5), 25.9 (Si-C-CH 3 ), 24.1 (C-6), 23.0 (C-7), 22.5 (C-7), 21.6 (SO 2 -Ar-CH 3 ), 18.3 (Si-C-CH 3 ), -4.3 (Si-CH 3 ), -4.4 (Si-CH 3 ); m/z (CI) 411 [MH] +, 220, 134, 117 (Found: [MH] +, C 22 H 38 O 3 SSi requires [MH] +, ). (1S,2R)-benzyl[1-isobutyl-2-(p-toluenesulfonylmethyl)but-3-enyl]carbamic acid tert-butyl ester 2m BocNBn R F 0.37 (30% ethyl acetate petrol); ν max (film) 2958, 2929, 2868, 1688(C=O), 1453, 1405, 1366, 1323 (SO 2 ), 1246, 1150 (SO 2 ), 922, 702 cm -1 ; δ H (270 MHz, CDCl 3 ) (9H, m, ortho SO 2 -Ar-CH 3, meta SO 2 -Ar-CH 3, Ph), (1H, m, H-2), (2H, m, CH 2-1), (3H, m, H-4, CH 2 -Ph), (1H, m, H-3), 2.42 (3H, s, SO 2 -Ar-CH 3 ), (14H, m, CH 2-5, H-6, CH 2 -SO 2 -Ar-CH 3, 3 C-CH 3 ), (6H, m, 2 CH 3-7); δ C (67.5 MHz, CDCl 3 ) (para C-Ar-OCH 3 ), (C=O), (C-2), 129.8, 129.7, 128.5, 128.5, 128.4, 128.3, 127.5, (ipso C-SO 2 -Ar-CH 3, ipso Ph, meta C-SO 2 -Ar- CH 3, meta Ph, ortho C-SO 2 -Ar-CH 3, ortho Ph, para Ph), (C-1), 77.3 (O-C-CH 3 ), 58.1 (CH 2 -Ph), 43.0 (CH 2 -SO 2 -Ar-CH 3 ), 42.7 (C-4), 38.9 (C-5), 30.4 (C-3), 28.5 (3 O-C-CH 3 ), 21.7 (SO 2 -Ar-CH 3 ); m/z (CI) 503 [M+NH 4 ] +,486 [MH] +, 288, 174, 94 (Found: [MH] +, C 28 H 39 NO 4 S requires [MH] +, ). 6
8 (±)-1-[2-(1-Phenylethyl)-but-3-ene-1-sulfonyl]-4-methyl-benzene 2n Me Ph ν max (film) 3080, 3028, 2968, 2925, 2875, 1597, 1452, 1314 (SO 2 ), 1300, 1183 (SO 2 ), 1087, 764 cm -1 ; δ H (270 MHz, CDCl 3 ) 7.67 (2H, d, J = 8.2 Hz, ortho SO 2 -Ar-CH 3 minor isomer), 7.60 (2H, d, J = 8.4 Hz, ortho SO 2 -Ar-CH 3 major isomer), (7H, m, meta SO 2 -Ar-CH 3, Ph), (1H, m, H-3), (2H, m, CH 2-4), (4H, m, CH 2-1, H-2, H-3'), 2.42 (3H, s, SO 2 -Ar-CH 3 ), 1.24 (3H, d, J = 7.2 Hz, CH 3-4' minor isomer), 1.13 (3H, d, J = 6.7 Hz, CH 3-4'major isomer); δ C (67.5 MHz, CDCl 3 ) (para SO 2 -Ar- CH 3 ), (ipso Ph), (C-3 major isomer), (C-3 minor isomer), (ipso SO 2 -Ar-CH 3 ), (meta SO 2 -Ar-CH 3 minor isomer), (meta SO 2 -Ar-CH 3 major isomer), (meta Ph major isomer), (meta Ph minor isomer), (ortho Ph minor isomer), (ortho Ph major isomer), (ortho SO 2 -Ar-CH 3 minor isomer), (ortho SO 2 -Ar-CH 3 major isomer), (para Ph), (C-4 major isomer), (C-4 minor isomer), 58.9 (C-1 major isomer), 58.6 (C-1 minor isomer), 45.6 (C-2 major isomer), 44.7 (C-2 major isomer), 43.5 (C-3' major isomer), 42.8 (C-3' major isomer), 21.7 (SO 2 -Ar-CH 3 ), 19.5 (C-4' major isomer), 18.0 (C-4' major isomer); m/z (CI) 332 [MNH 4 ] +, 315 [MH] +, 228, 159, 105 (Found: [MH] +, C 19 H 22 SO 2 requires [MH] +, ). 7
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