Asymmetric [2,3]sigmatropic rearrangement of chiral allylic selenimides

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 2932-2933

  Kurose, Noriyuki ^a   Takahashi, Tamiko ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000332081     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960287b     Document Type: Article

References (16)

1. For asymmetric [2,3]sigmatropic rearrangement of chiral selenoxides: (a) Nishibayashi, Y.; Singh, J. D.; Fukuzawa, S.; Uemura, S. J. Org. Chem. 1995, 60, 4114. (b) Komatsu, N.; Nishibayashi, Y.; Uemura, S. Tetrahedron Lett. 1993, 34, 2339. (c) Davis, F. A.; Reddy, R. T. J. Org. Chem. 1992, 57, 2599. (d) Reich, H. J.; Yelm, K. E. J. Org. Chem. 1991, 56, 5672. For asymmetric β-elimination of chiral selenoxides: ref 1a and references cited therein.
2. For asymmetric [2,3]sigmatropic rearrangement of chiral selenoxides: (a) Nishibayashi, Y.; Singh, J. D.; Fukuzawa, S.; Uemura, S. J. Org. Chem. 1995, 60, 4114. (b) Komatsu, N.; Nishibayashi, Y.; Uemura, S. Tetrahedron Lett. 1993, 34, 2339. (c) Davis, F. A.; Reddy, R. T. J. Org. Chem. 1992, 57, 2599. (d) Reich, H. J.; Yelm, K. E. J. Org. Chem. 1991, 56, 5672. For asymmetric β-elimination of chiral selenoxides: ref 1a and references cited therein.
3. For asymmetric [2,3]sigmatropic rearrangement of chiral selenoxides: (a) Nishibayashi, Y.; Singh, J. D.; Fukuzawa, S.; Uemura, S. J. Org. Chem. 1995, 60, 4114. (b) Komatsu, N.; Nishibayashi, Y.; Uemura, S. Tetrahedron Lett. 1993, 34, 2339. (c) Davis, F. A.; Reddy, R. T. J. Org. Chem. 1992, 57, 2599. (d) Reich, H. J.; Yelm, K. E. J. Org. Chem. 1991, 56, 5672. For asymmetric β-elimination of chiral selenoxides: ref 1a and references cited therein.
4. For asymmetric [2,3]sigmatropic rearrangement of chiral selenoxides: (a) Nishibayashi, Y.; Singh, J. D.; Fukuzawa, S.; Uemura, S. J. Org. Chem. 1995, 60, 4114. (b) Komatsu, N.; Nishibayashi, Y.; Uemura, S. Tetrahedron Lett. 1993, 34, 2339. (c) Davis, F. A.; Reddy, R. T. J. Org. Chem. 1992, 57, 2599. (d) Reich, H. J.; Yelm, K. E. J. Org. Chem. 1991, 56, 5672. For asymmetric β-elimination of chiral selenoxides: ref 1a and references cited therein.
5. Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 59, 3262.
6. Takahashi, T.; Kurose, N.; Kawanami, S.; Arai, Y.; Koizumi, T.; Shiro, M. J. Org. Chem. 1994, 59, 3262.
7. Se)-selenonium ylides exclusively: Takahashi, T.; Kurose, N.; Kawanami, S.; Nojiri, A.; Arai, Y.; Koizumi, T.; Shiro, M. Chem. Lett. 1995, 379.
8. We have applied this selenoxide to an asymmetric protonation reaction: Takahashi, T.; Nakao, N ; Koizumi, T. Chem. Lett. 1996, 207.
9. Poth, N. Rev. Tech. Luxemb. 1976, 68, 195; Chem. Abstr. 1977, 87, 135965k.
10. Poth, N. Rev. Tech. Luxemb. 1976, 68, 195; Chem. Abstr. 1977, 87, 135965k.
11. Syper, L.; Młochowski, J. Synthesis 1984, 439.
12. Scaborough, R. M., Jr.; Toder, B. H.; Smith, A. B., III. J. Am. Chem. Soc. 1980, 102, 3904.
13. 3.7]decane (ref 3).
14. Moriwake, T.; Hamano, S.; Saito, S.; Torii, S.; Kashino, S. J. Org. Chem. 1989, 54, 4114.
15. Uemura et al. have obtained 11c in 87% ee. Its absolute configuration has not been reported (ref 2).
16. ent-7 was prepared from (1R)-10-camphorsulphonic acid according to the method for the synthesis of 7 in 29% overall yield.