The first example of enantioselective protonation of prochiral enolates with chiral γ-hydroxyselenoxides

Chemistry Letters

Volumn , Issue 3, 1996, Pages 207-208

  Takahashi, Tamiko ^a   Nakao, Naoki ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030528828     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.207     Document Type: Article

References (11)

1. "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1983), Vol. 2 and (1984), Vol. 3.
2. N. Komatsu and S. Uemura, Synth. Org. Chem., 53, 268 (1995), and references cited therein.
3. T. Takahashi, N. Kurose, S. Kawanami, Y. Arai, T. Koizumi, and M. Shiro, J. Org. Chem., 59, 3262 (1994).
4. 13C NMR, Mass) data were obtained for all new compounds.
5. Enantiomer excess of compound 8 was calculated from [α]o value using +46.5 degree of pure (R)-8 as a standard reported by Meyers et al.: A. I. Meyers, D. R. Williams, G. W. Erickson, S. White, and M. Druelinger, J. Am. Chem. Soc., 103, 3081 (1981).
6. K. Matsumoto and H. Ohta, Tetrahedron Lett., 32, 4729 (1991).
7. House et al. have reported that a directed aldol condensation proceeds in highly stereoselective manner by using a zinc halide enolate: R. A. Auerbach, D. S. Crumrine, D. L. Ellison, and H. O. House, in "Organic Syntheses," Wiley, New York (1988), Collect. Vol. VI, p. 692.
8. Enantiomer excess of compound 10 was determined by HPLC analysis with CHIRALCEL OB (Daisel Chemical Industries, Ltd.). Absolute configuration of 10 was determined by comparing the sign of optical rotation with reported one: A. I. Meyers, D. R. Williams, and M. Druelinger, J. Am. Chem. Soc., 98, 3032 (1976).
9. a) K. Hoshino, H. Kosugi, and H. Uda, The Book of Abstracts of 20th Symposium on Heteroatom Chemistry, Tokyo, 1993, p. 5.
10. b) H. Kosugi, K. Hoshino, H. Kohno, R. Hatsuda, and H. Uda, The Book of Abstracts of 22nd Symposium on Heteroatom Chemistry, Nagoya, 1995, p. 93.
11. c) A. Yanagisawa, T. Kikuchi, T. Watanabe, T. Kuribayashi; and H. Yamamoto, Synlett, 1995, 372, and references cited therein.