BINAP/AgOTf/KF/18-Crown-6 as New Bifunctional Catalysts for Asymmetric Sakurai−Hosomi Allylation and Mukaiyama Aldol Reaction

Manabu Wadamoto,†§ Nobuko Ozasa,† Akira Yanagisawa,‡ and Hisashi Yamamoto*†§
Graduate School of Engineering, Nagoya University, SORST, Japan Science and Technology Corporation (JST), Chikusa, Nagoya 464-8603, Japan, and Department of Chemistry, Faculty of Science, Chiba University, Inage, Chiba 263-8522, Japan
J. Org. Chem., 2003, 68 (14), pp 5593–5601
DOI: 10.1021/jo020691c
Publication Date (Web): June 19, 2003
Copyright © 2003 American Chemical Society
†

 Graduate School of Engineering, Nagoya University, SORST.

,
§

 Current address:  Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637.

,
‡

 Department of Chemistry, Faculty of Science, Chiba University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, yamamoto@uchicago.edu

Abstract

Abstract Image

A catalytic amount of KF·18-crown-6 complex is effective as a soluble fluoride source to activate an asymmetric Sakurai−Hosomi allylation with BINAP and silver(I) triflate catalyst. The allylation of a variety of aromatic, α,β-unsaturated and aliphatic aldehydes with allylic trimethoxysilane resulted in high yields and remarkable enantioselectivities. In addition, the asymmetric Mukaiyama-type aldol reaction is achieved by using trimethoxysilyl enol ethers in the presence of the same catalysts. High anti selectivity is obtained from E-silyl enol ether, while Z-silyl enol ether gives syn selectivity.

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History

  • Published In Issue July 11, 2003
  • Received November 11, 2002

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