Asymmetric reductive cyclization using the intramolecular conjugate addition of enolates onto α,β-unsaturated sulfoxides

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 47-50

  Yoshizaki, Hiroki ^a   Tanaka, Tadashi ^a   Yoshii, Eiichi ^a   Koizumi, Toru ^a   Takeda, Kei ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; SULFOXIDE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; REDUCTION;

EID: 0031983242     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10414-2     Document Type: Article

References (12)

1. (a) Yoshii, E.; Hori, K.; Nomura, K.; Yamaguchi, K. Synlett 1995, 568-570.
2. (b) Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888-2902.
3. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc., New York, 1995.
4. For asymmetric nucleophilic addition to electron deficient alkenes, see: Schmalz, H-G. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp. 199-236.
5. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon Press Ltd., Oxford, 1992.
6. For intermolecular asymmetric Michael additions of ester enolates to doubly-activated vinylsulfoxides, see: a) Posner, G.H.; Weitzberg, M.; Hamill, T.G.; Asirvatham, E.; Cun-Heng H.; Clardy, J. Tetrahedron 1986, 42, 2919-2929. Also, see
7. (b) Posner, G.H. Acc. Chem. Res. 1987, 20, 72-78.
8. (c) Koizumi, T. J. Synth. Org. Chem. Jpn. 1986, 44, 576-590.
9. Kosugi H., Kitaoka M., Tagami K., Takahashi A., Uda H. J. Org. Chem. 52:1987;1078-1082.
10. 3, R = 3.6 for 2144 reflections. Diffraction data were collected on a Rigaku AFC7R diffractometer with graphite monochromated Mo-Ka radiation and 12 kW rotating generator. The structure was solved by the direct methods and expanded using Fourier techniques.
11. 3). The 1,2-cis-relationship was secured by NOESY experiments.
12. 3).