Asymmetric synthesis of sultams and sulfonamides via diastereoselective reduction of N-sulfonylimines

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 115, Issue , 1996, Pages 85-91

  Davis, Franklin A ^a   Zhou, Ping ^b   Chen, Bang Chi ^b  

^a Temple University   (United States)

^b DREXEL UNIVERSITY   (United States)

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Chiral nonracemic sulfonamides; Diastereoselective reduction; Sultams

Indexed keywords

EID: 0030495691     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509608037955     Document Type: Article

References (18)

1. F. A. Davis, P. Zhou and C. K. Murphy, Tetrahedron Lett., 34, 3971 (1993).
2. For reviews on camphorsultam 1a in organic synthesis see: W. Oppolzer, Tetrahedron, 43, 1969 (1987); W. Oppolzer, Pure Appl. Chem., 62, 1241 (1990); B. H. Kim and D. P. Curran, Tetrahedron, 49, 293 (1992).
3. For reviews on camphorsultam 1a in organic synthesis see: W. Oppolzer, Tetrahedron, 43, 1969 (1987); W. Oppolzer, Pure Appl. Chem., 62, 1241 (1990); B. H. Kim and D. P. Curran, Tetrahedron, 49, 293 (1992).
4. For reviews on camphorsultam 1a in organic synthesis see: W. Oppolzer, Tetrahedron, 43, 1969 (1987); W. Oppolzer, Pure Appl. Chem., 62, 1241 (1990); B. H. Kim and D. P. Curran, Tetrahedron, 49, 293 (1992).
5. R. L. Shringer, J. A. Shotten and H. Sutherland, J. Am. Chem. Soc., 60, 2794 (1938).
6. M. C. Weismiller, J. C. Towson and F. A. Davis, Org. Synth., 69, 154 (1990); M. C. Weismiller, J. C. Towson and F. A. Davis, Org. Synth., Coll. Vol. VIII, 110 (1993).
7. M. C. Weismiller, J. C. Towson and F. A. Davis, Org. Synth., 69, 154 (1990); M. C. Weismiller, J. C. Towson and F. A. Davis, Org. Synth., Coll. Vol. VIII, 110 (1993).
8. (a) For dehalogenations under catalytic hydrogenation conditions, see: L. J. Sargent and J. H. Ager, J. Org. Chem., 23, 1938 (1958); K. Luthman, M. Orbe, T. Waglund and A. Claesson, J. Org. Chem., 52, 3777 (1987);
9. (a) For dehalogenations under catalytic hydrogenation conditions, see: L. J. Sargent and J. H. Ager, J. Org. Chem., 23, 1938 (1958); K. Luthman, M. Orbe, T. Waglund and A. Claesson, J. Org. Chem., 52, 3777 (1987);
10. (b) For lithium aluminum hydride mediated dehalogenation, see: P. Kulanthaivel and S. W. Pelletier, Tetrahedron Lett., 28, 3883 (1987); S. Krishnamurthy and H. C. Brown, J. Org. Chem., 47, 276 (1982).
11. (b) For lithium aluminum hydride mediated dehalogenation, see: P. Kulanthaivel and S. W. Pelletier, Tetrahedron Lett., 28, 3883 (1987); S. Krishnamurthy and H. C. Brown, J. Org. Chem., 47, 276 (1982).
12. For a recent reference on the reduction of camphor imines with sodium boron hydride, see: R. Bolton, T. N. Danks and J. M. Paul, Tetrahedron Lett., 35, 3411 (1994).
13. For a general review on the asymmetric reduction of imines see: Q.-C. Zhu, R. O. Hutchins and M. K. Hutchins, Org. Prep. Proced. Int., 26, 193 (1994).
14. F. A. Davis, M. C. Weismiller, C. K. Murphy, R. T. Reddy and B.-C. Chen, J. Org. Chem., 57, 7274 (1992).
15. F. A. Davis, P. Zhou and P. J. Carroll, J. Org. Chem., 58, 4890 (1993).
16. W. Oppolzer, C. Chpuis and G. Bernardinelli, Tetrahedron Lett., 25, 5885 (1984).
17. (a) J. C. Towson, M. C. Weismiller, S. G. Lal, A. C. Sheppard and F. A. Davis, Org. Synth., 69, 158 (1990);
18. (b) B.-C. Chen, C. K. Murphy, A Kumar, R. ThimmaReddy, P. Zhou, B. M. Lewis, D. Gala, I. Mergelsberg, D. Scherer, J. Duckley, D. Didenedetto and F. A. Davis, Org. Synth., 73, 159 (1995).