Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
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1 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
2 A new route to enantiopure b-aryl-substituted b-amino acids and 4-aryl-substituted b-lactams through lipase-catalyzed enantioselective ring cleavage of b-lactams Eniko Forró, Ferenc Fülöp* Institute of Pharmaceutical Chemistry, University of Szeged, H-6701 Szeged, P Box 427, Hungary Supporting Information The spectroscopic and analytical data for compounds (±)-1- (±)-7 (Scheme 1) 1. CSI (±)-1 = H (±)-2 = p-me (±)-3 = o-cl (±)-4 = m-cl (±)-5 = p-cl (±)-6 = p-br (±)-7 = p-f 2. Na 2 S % (±)-8 = H (±)-9 = p-me (±)-10 = o-cl (±)-11 = m-cl (±)-12 = p-cl (±)-13 = p-br (±)-14 = p-f Scheme 1 (±)-4-Phenyl-2-azetidinone, (±)-1: 1 H NM (400 MHz, CDCl 3 ) δ (ppm): (1H, dd, J = 2, 14.8, CH A H) (1H, ddd, J = 2.4; 5.2; 7.6, CH B H), (1H, dd, J = 2.5; 5.3, CH), 6.34 (1H, bs, ) (5H, m, Ph). 13 C NM ( MHz, CDCl 3 ) δ (ppm) 48.6, 51.0, 126.3, 128.8, 129.5, 140.9, Analysis: calculated for C 9 H 9 N: C, 73.45; H, 6.16; N, 9.52; found: C, 73.42; H, 6.00; N, (±)-4-(p-Tolyl)-2-azetidinone, (±)-2: (1.73 g, 63%; mp C, lit. [7] mp C). 1 H NM (400 MHz, CDCl 3 ) δ (ppm): 2.35 (3H, s, CH 3 ) (1H, dd, J = 1.7; 14.8, CH A H) (1H, ddd, J = 2.4; 5.2; 7.6, CH B H), (1H, dd, J = 2.3; 5.2, CH), 6.13 (1H, bs, ) (4H, m, Ph). 13 C NM ( MHz, CDCl 3 ) δ (ppm) 21.8, 48.7, 50.9, 126.3, 130.2, 137.8, 138.7, Analysis: calculated for C 10 H 11 N: C, 74.51; H, 6.88; N, 8.69; found: C, 74.66; H, 6.83; N, (±)-4-(2-Chlorophenyl)-2-azetidinone, (±)-3: 1 H NM (400 MHz, CDCl 3 ) d (ppm): (1H, dd, J = 2.6; 14.9, CH A H), (1H, ddd, J = 2.9; 5.4; 8.3, CH B H), (1H, dd, J = 2.6; 5.4, CH), 6.33 (1H, bs, ), (4H, m, Ph). 13 C NM ( MHz, CDCl 3 ) δ (ppm) 47.4, 48.7, 126.6, 127.8, 129.7, 130.3, 133.2, 138.4, Analysis: calculated for C 9 H 8 ClN: C, 59.52; H, 4.44; N, 7.71; found: C, 59.34; H, 4.41; N, (±)-4-(3-Chlorophenyl)-2-azetidinone, (±)-4: 1 H NM (400 MHz, CDCl 3 ) d (ppm): (1H, dd, J = 2.0; 14.9, CH A H), (1H, ddd, J = 2.6; 5.3; 14.9, CH B H), (1H, dd, J = 2.4; 5.3, CH), 6.20 (1H, bs, ), (4H, m, Ph). 13 C NM ( MHz, CDCl 3 ) δ (ppm) 48.6, 50.5, 124.4, 126.5, 128.9, 130.8, 135.5, 143.1, Analysis: calculated for C 9 H 8 ClN: C, 59.52; H, 4.44; N, 7.71; found: C, 59.51; H, 4.30 N, (±)-4-(4-Chlorophenyl)-2-azetidinone, (±)-5: 1 H NM (400 MHz, CDCl 3 ) d (ppm): (1H, dd, J = 1.8; 14.9, CH A H), (1H, ddd, J = 2.6; 5.3; 14.9, CH B H), (1H, dd, J = 2.4; 5.2, CH), 6.30 (1H, bs, ), (4H, m, Ph). 13 C NM ( MHz,
3 CDCl 3 ) δ (ppm) 48.7, 50.4, 127.7, 129.7, 134.6, 139.4, Analysis: calculated for C 9 H 8 ClN: C, 59.52; H, 4.44; N, 7.71; found: C, 59.50; H, 4.35; N, (±)-4-(4-Bromophenyl)-2-azetidinone, (±)-6: 1 H NM (400 MHz, CDCl 3 ) d (ppm): (1H, dd, J = 2.0; 14.9, CH A H), (1H, ddd, J = 2.6; 5.3; 7.9, CH B H), (1H, dd, J = 2.5; 5.3, CH), 6.24 (1H, bs, ), (4H, m, Ph). 13 C NM ( MHz, CDCl 3 ) δ (ppm) 48.6, 50.5, 122.7, 128.0, 132.6, 139.9, Analysis: calculated for C 9 H 8 BrN: C, 47.82; H, 3.57; N, 6.20; found: C, 47.76; H, 3.47; N, (±)-4-(4-Fluorophenyl)-2-azetidinone, (±)-7: 1 H NM (400 MHz, CDCl 3 ) d (ppm): (1H, ddd, J = 0.8; 2.5; 14.9, CH A H), (1H, ddd, J = 2.6; 5.3; 14.9, CH B H), (1H, dd, J = 2.5; 5.3, CH), 6.26 (1H, bs, ), (4H, m, Ph). 13 C NM ( MHz, CDCl 3 ) δ (ppm) 48.7, 50.4, 116.3, 116.5, 127.9, 128.0, 136.6, 164.4, Analysis: calculated for C 9 H 8 FN: C, 65.45; H, 4.88; N, 8.48; found: C, 65.34; H, 4.85; N, The spectroscopic and analytical data for enantiopure compounds (Scheme 2) (±)-1 = H (±)-2 = p-me (±)-3 = o-cl (±)-4 = m-cl (±)-5 = p-cl (±)-6 = p-br (±)-7 = p-f CAL-B H 2 ipr 2 60 C CH 2 ()-15 = H ()-16 = p-me ()-17 = o-cl ()-18 = m-cl ()-19 = p-cl ()-20 = p-br ()-21 = p-f 22% HCl/EtH CH. 2 HCl + S HN (S)-22 = H (S)-23 = p-me (S)-24 = o-cl (S)-25 = m-cl (S)-26 = p-cl (S)-27 = p-br (S)-28 = p-f HC HCl. H 2 N 18% HCl D S ()-29 = H ()-30 = p-me ()-31 = o-cl ()-32 = m-cl ()-33 = p-cl ()-34 = p-br ()-35 = p-f Scheme 2 (S)-36 = H (S)-37 = p-me (S)-38 = o-cl (S)-39 = m-cl (S)-40 = p-cl (S)-41 = p-br (S)-42 = p-f ()-15: 1 H NM (400 MHz, D 2 ) δ (ppm): (2H, m, CH 2 ), (1H, m, CH), (5H, m, Ph). Analysis: calculated for C 9 H 11 N 2 : C, 65.44; H, 6.71; N, 8.48; found: C, 65.41; H, 6.58; N, ()-16: 1 H NM (400 MHz, D 2 ) δ (ppm): 2.35 (3H, s, CH 3 ), (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 10 H 13 N 2 : C, 67.02; H, 7.31; N, 7.82; found: C, 66.83; H, 7.33; N, ()-17: 1 H NM (400 MHz, D 2 ) δ (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 ClN 2 : C, 54.15; H, 5.05; N, 7.02; found: C, 54.06; H, 5.17; N, ()-18: 1 H NM (400 MHz, D 2 ) δ (ppm): 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 ClN 2 : C, 54.15; H, 5.05; N, 7.02; found: C, 54.37; H, 5.27; N, ()-19: 1 H NM (400 MHz, D 2 ) δ (ppm): 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 ClN 2 : C, 54.15; H, 5.05; N, 7.02; found: C, 54.23; H, 4.88; N, 6.94.
4 ()-20: 1 H NM (400 MHz, D 2 ) δ (ppm): 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 BrN 2 : C, 44.29; H, 4.13; N 5.74; found: C, 44.08; H, 4.13; N ()-21: 1 H NM (400 MHz, D 2 ) δ (ppm): 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 FN 2 : C, 59.01; H, 5.50; N 7.65; found: C, 58.88; H, 5.54; N (S)-22: The 1 H NM (400 MHz, CDCl 3 ) δ (ppm) data are similar to those for (±)-1. Analysis: calculated for C 9 H 9 N: C, 73.45; H, 6.16; N, 9.52; found: 73.37; H, 6.08; N, (S)-23: The 1 H NM (400 MHz, CDCl 3 ) δ (ppm) data are similar to those for (±)-2. Analysis: calculated for C 10 H 11 N: C, 74.51; H, 6.88; N, 8.69; found: C, 74.55; H, 6.65; N, (S)-24: The 1 H NM (400 MHz, CDCl 3 ) δ (ppm) data are similar to those for (±)-3. Analysis: calculated for C 9 H 8 ClN: C, 59.52; H, 4.44; N, 7.71; found: C, 59.66; H, 4.35; N, (S)-25: The 1 H NM (400 MHz, CDCl 3 ) δ (ppm) data are similar to those for (±)-4. Analysis: calculated for C 9 H 8 ClN: C, 59.52; H, 4.44; N, 7.71; found: C, 59.61; H, 4.38; N, (S)-26: The 1 H NM (400 MHz, CDCl 3 ) δ (ppm) data are similar to those for (±)-5. Analysis: calculated for C 9 H 8 ClN: C, 59.52; H, 4.44; N, 7.71; found: C, 59.59; H, 4.39; N, (S)-27: The 1 H NM (400 MHz, CDCl 3 ) δ (ppm) data are similar to those for (±)-6. Analysis: calculated for C 9 H 8 BrN: C, 47.82; H, 3.57; N, 6.20; found: C, 47.97; H, 3.55; N, (S)-28: The 1 H NM (400 MHz, CDCl 3 ) δ (ppm) data are similar to those for (±)-7. Analysis: calculated for C 9 H 8 FN: C, 65.45; H, 4.88; N, 8.48; found: C, 65.59; H, 4.67; N, ()-29: 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (5H, m, Ph). Analysis: calculated for C 9 H 11 N 2 HCl: C, 53.61; H, 6.00; N, 6.95; found: C, 53.47; H, 6.09; N, ()-30: 1 H NM (400 MHz, D 2 ) δ (ppm): 2.34 (3H, s, CH 3 ), (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 10 H 13 N 2 HCl: C, 55.69; H, 6.54; N, 6.49; found: C, 55.72; H, 6.50; N, ()-31: 1 H NM (400 MHz, D 2 ) δ (ppm): 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 ClN 2 HCl: C, 45.79; H, 4.70; N, 5.93; found: C, 45.65; H, 4.74; N, ()-32: 1 H NM (400 MHz, D 2 ) δ (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 ClN 2 HCl: C, 45.79; H, 4.70; N, 5.93; found: C, 45.64; H, 4.60; N, ()-33: 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 ClN 2 HCl: C, 45.79; H, 4.70; N, 5.93; found: C, 45.76; H, 4.66; N, ()-34: 1 H NM (400 MHz, D 2 ) δ (ppm): 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 BrN 2 HCl: C, 38.53; H, 3.95; N, 4.99; found: C, 38.68; H, 4.10; N, ()-35: 1 H NM (400 MHz, D 2 ) δ (ppm): 1 H NM (400 MHz, D 2 ) d (ppm): (2H, m, CH 2 ), (1H, m, CH), (4H, m, Ph). Analysis: calculated for C 9 H 10 FN 2 HCl: C, 49.22; H, 5.05; N, 6.38; found: C, 49.10; H, 5.16; N, (S)-36: The 1 H NM (400 MHz, H 2 ) δ (ppm) data are similar to those for ()-29. Analysis: calculated for C 9 H 11 N 2 HCl: C, 53.61; H, 6.00; N, 6.95; found: C, 53.43; H, 6.01; N, (S)-37: The 1 H NM (400 MHz, H 2 ) δ (ppm) data are similar to those for ()-30. Analysis: calculated for C 10 H 13 N 2 HCl: C, 55.69; H, 6.54; N, 6.49; found: C, 55.64; H, 6.37; N, (S)-38: The 1 H NM (400 MHz, H 2 ) δ (ppm) data are similar to those for ()-31. Analysis: calculated for C 9 H 10 ClN 2 HCl: C, 45.79; H, 4.70; N, 5.93; found: C, 45.61; H, 4.70; N, 5.65.
5 (S)-39: The 1 H NM (400 MHz, H 2 ) δ (ppm) data are similar to those for ()-32. Analysis: calculated for C 9 H 10 ClN 2 HCl: C, 45.79; H, 4.70; N, 5.93; found: C, 45.68; H, 4.55; N, (S)-40: The 1 H NM (400 MHz, H 2 ) δ (ppm) data are similar to those for ()-33. Analysis: calculated for C 9 H 10 ClN 2 HCl: C, 45.79; H, 4.70; N, 5.93; found: C, 45.77; H, 4.61; N, (S)-41: The 1 H NM (400 MHz, H 2 ) δ (ppm) data are similar to those for ()-34. Analysis: calculated for C 9 H 10 BrN 2 HCl: C, 38.53; H, 3.95; N, 4.99; found: C, 38.37; H, 3.90; N, (S)-42: The 1 H NM (400 MHz, H 2 ) δ (ppm) data were similar to those for ()-35. Analysis: calculated for C 9 H 10 FN 2 HCl: C, 49.22; H, 5.05; N, 6.38; found: C, 49.07; H, 4.92; N, 6.40.
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