Practical Synthesis of Chiral Sultam Auxiliaries: 3-Substituted-1,2-benzisothiazoline 1,1-Dioxides

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 7047-7048

  Ahn, Kyo Han ^a   Ham, Cheol ^a   Kim, Seung Kee ^a   Cho, Chang Woo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZISOTHIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROGENATION; SYNTHESIS;

EID: 0000290050     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970917p     Document Type: Article

References (17)

1. (a) Oppolzer, W.; Wills, M.; Starkemann, C.; Bemardinelli, G. Tetrahedron Lett. 1990, 31, 4117.
2. (b) Oppolzer, W.; Wills, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015.
3. (c) Oppolzer, W.; Rodriguez, I.; Starkemann, C.; Walther, E. Tetrahedron Lett. 1990, 31, 5019.
4. (d) Oppolzer, W.; Kingma, A. J.; Pillai, S. K. Tetrahedron Lett. 1991, 32, 4893. An attempted asymmetric hydrogenation of 5b under the same conditions that were used for the synthesis of 1 gave only traces of racemic sultam 2.
5. (a) Oppolzer, W. Tetrahedron 1987, 43, 1969.
6. (b) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241.
7. (a) Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065.
8. (b) Ahn, K. H.; Yoo, D. J.; Kim, J. S. Tetrahedron Lett. 1992, 33, 6661.
9. Kitamura, M.; Tokunaga, M.; Noyori, R. J. Org. Chem. 1992, 57, 4053.
10. Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett. 1991, 32, 4163.
11. (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
12. (b) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916.
13. R-Description for this (-)-2 in the literature should be corrected to S according to the sequence rule: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons, Inc.: New York, 1994; pp 101-112.
14. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
15. The solvent must be degassed by flushing with an inert gas; otherwise, the dimerization of benzyl Grignard reagent significantly reduces the addition yield. For the addition of Grignard reagents to saccharin, see; Abramovitch, R. A.; Smith, E. M.; Humber, M.; Purtschert, B.; Srinivasan, P. C.; Singer, G. M. J. Chem. Soc., Perkin Trans. I 1974, 2589.
16. The authors have deposited atomic coordinates for 6 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
17. 2 pressure has been reported; see: Charette, A. B.; Giroux, A. Tetrahedron Lett. 1996, 37, 6669.