Self-condensation of N-tert-butanesulfinyl aldimines: Application to the rapid asymmetric synthesis of biologically important amine-containing compounds

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3621-3624

  Schenkel, Laurie B ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOCYCLOPENTANECARBOXYLIC ACID; 4 AMINO 5 CHLORO N [(HEXAHYDRO 1H PYRROLIZIN 1 YL)METHYL] 2 METHOXYBENZAMIDE; AMINE; IMINE;

ARTICLE; DRUG SYNTHESIS; MICROWAVE RADIATION; POLYMERIZATION; QUANTUM YIELD;

AMINES; BENZAMIDES; CATALYSIS; INDICATORS AND REAGENTS; MICROWAVES; MOLECULAR STRUCTURE; NITRILES; PYRROLES;

EID: 6444233585     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048458j     Document Type: Article

References (40)

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27. tert-Butanesulfinamides also undergo concerted eliminations of tert-butanesulfenic acid to provide unsubstituted imines, but this transformation apparently has a higher activation barrier than for conversion of N-tert-butanesulfinyl imines to nitriles.
28. For other asymmetric syntheses, see: (a) LePlae, P. R.; Umezawa, N.; Lee, H.-S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (b) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253. (c) Enders, D.; Weidemann, J. Liebigs Ann./Recueil 1997, 699. (d) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411. (e) Perlmutter, P.; Rose, M.; Vounatsos, F. Eur. J. Org. Chem. 2003, 756.
29. For other asymmetric syntheses, see: (a) LePlae, P. R.; Umezawa, N.; Lee, H.-S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (b) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253. (c) Enders, D.; Weidemann, J. Liebigs Ann./Recueil 1997, 699. (d) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411. (e) Perlmutter, P.; Rose, M.; Vounatsos, F. Eur. J. Org. Chem. 2003, 756.
30. For other asymmetric syntheses, see: (a) LePlae, P. R.; Umezawa, N.; Lee, H.-S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (b) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253. (c) Enders, D.; Weidemann, J. Liebigs Ann./Recueil 1997, 699. (d) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411. (e) Perlmutter, P.; Rose, M.; Vounatsos, F. Eur. J. Org. Chem. 2003, 756.
31. For other asymmetric syntheses, see: (a) LePlae, P. R.; Umezawa, N.; Lee, H.-S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (b) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253. (c) Enders, D.; Weidemann, J. Liebigs Ann./Recueil 1997, 699. (d) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411. (e) Perlmutter, P.; Rose, M.; Vounatsos, F. Eur. J. Org. Chem. 2003, 756.
32. For other asymmetric syntheses, see: (a) LePlae, P. R.; Umezawa, N.; Lee, H.-S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (b) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253. (c) Enders, D.; Weidemann, J. Liebigs Ann./Recueil 1997, 699. (d) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411. (e) Perlmutter, P.; Rose, M.; Vounatsos, F. Eur. J. Org. Chem. 2003, 756.
33. Representative examples include: (a) Flynn, D. L.; Zabrowski, D. L.; Becker, D. P.; Nosal, R.; Villamil, C. I.; Gullikson, G. W.; Moummi, C.; Yang, D.-C. J. Med. Chem. 1992, 35, 1489. (b) Becker, D. P.; Flynn, D. L.; Villamil, C. I. Biorg. Med. Chem. Lett. 2004, 14, 3073. (c) Zabrowski, D. L.; Flynn, D. L. U.S. Patent 4,992,461, 1989. (d) Becker, D. P.; Flynn, D. L.; Moormann, A. E.; Nosal, R.; Villamil, C. I. U.S. Patent 5,137,893, 1991.
34. Representative examples include: (a) Flynn, D. L.; Zabrowski, D. L.; Becker, D. P.; Nosal, R.; Villamil, C. I.; Gullikson, G. W.; Moummi, C.; Yang, D.-C. J. Med. Chem. 1992, 35, 1489. (b) Becker, D. P.; Flynn, D. L.; Villamil, C. I. Biorg. Med. Chem. Lett. 2004, 14, 3073. (c) Zabrowski, D. L.; Flynn, D. L. U.S. Patent 4,992,461, 1989. (d) Becker, D. P.; Flynn, D. L.; Moormann, A. E.; Nosal, R.; Villamil, C. I. U.S. Patent 5,137,893, 1991.
35. Representative examples include: (a) Flynn, D. L.; Zabrowski, D. L.; Becker, D. P.; Nosal, R.; Villamil, C. I.; Gullikson, G. W.; Moummi, C.; Yang, D.-C. J. Med. Chem. 1992, 35, 1489. (b) Becker, D. P.; Flynn, D. L.; Villamil, C. I. Biorg. Med. Chem. Lett. 2004, 14, 3073. (c) Zabrowski, D. L.; Flynn, D. L. U.S. Patent 4,992,461, 1989. (d) Becker, D. P.; Flynn, D. L.; Moormann, A. E.; Nosal, R.; Villamil, C. I. U.S. Patent 5,137,893, 1991.
36. Representative examples include: (a) Flynn, D. L.; Zabrowski, D. L.; Becker, D. P.; Nosal, R.; Villamil, C. I.; Gullikson, G. W.; Moummi, C.; Yang, D.-C. J. Med. Chem. 1992, 35, 1489. (b) Becker, D. P.; Flynn, D. L.; Villamil, C. I. Biorg. Med. Chem. Lett. 2004, 14, 3073. (c) Zabrowski, D. L.; Flynn, D. L. U.S. Patent 4,992,461, 1989. (d) Becker, D. P.; Flynn, D. L.; Moormann, A. E.; Nosal, R.; Villamil, C. I. U.S. Patent 5,137,893, 1991.
37. For representative natural product syntheses, see: (a) Ledoux, S.; Marchalant, E.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 5397. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Eur. J. Org. Chem. 2000, 2227. (c) David, O.; Blot, J.; Bellec, C.; Fargeau-Bellassoued, M.-C.; Haviari, G.; Célérier, J.-P.; Lhommet, G.; Gramain, J.-C.; Gardette, D. J. Org. Chem. 1999, 64, 3122. (d) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Org. Chem. 1990, 55, 1148.
38. For representative natural product syntheses, see: (a) Ledoux, S.; Marchalant, E.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 5397. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Eur. J. Org. Chem. 2000, 2227. (c) David, O.; Blot, J.; Bellec, C.; Fargeau-Bellassoued, M.-C.; Haviari, G.; Célérier, J.-P.; Lhommet, G.; Gramain, J.-C.; Gardette, D. J. Org. Chem. 1999, 64, 3122. (d) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Org. Chem. 1990, 55, 1148.
39. For representative natural product syntheses, see: (a) Ledoux, S.; Marchalant, E.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 5397. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Eur. J. Org. Chem. 2000, 2227. (c) David, O.; Blot, J.; Bellec, C.; Fargeau-Bellassoued, M.-C.; Haviari, G.; Célérier, J.-P.; Lhommet, G.; Gramain, J.-C.; Gardette, D. J. Org. Chem. 1999, 64, 3122. (d) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Org. Chem. 1990, 55, 1148.
40. For representative natural product syntheses, see: (a) Ledoux, S.; Marchalant, E.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 5397. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Eur. J. Org. Chem. 2000, 2227. (c) David, O.; Blot, J.; Bellec, C.; Fargeau-Bellassoued, M.-C.; Haviari, G.; Célérier, J.-P.; Lhommet, G.; Gramain, J.-C.; Gardette, D. J. Org. Chem. 1999, 64, 3122. (d) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Org. Chem. 1990, 55, 1148.