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Silver-Catalyzed Asymmetric Sakurai-Hosomi Allylation of Ketones

Manabu Wadamoto and Hisashi Yamamoto*

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, Email: yamamotouchicago.edu

M. Wadamoto, H. Yamamoto, J. Am. Chem. Soc., 2005, 127, 14556-14557.

DOI: 10.1021/ja0553351 (free Supporting Information)


Abstract

AgF and (R)-DIFLUORPHOS predominantly formed a 1:1 complex that provided high enantioselectivity for the asymmetric Sakurai-Hosomi allylation of various simple ketones. Only 1,2-adducts were obtained from both acyclic and cyclic conjugate ketones. Highly diastereo- and enantioselective reactions with E- or Z-crotyltrimethoxysilane and racemic allylsilanes are described.

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

M. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem., 2003, 68, 5593-5601.


Key Words

Hosomi-Sakurai Reaction, Homoallylic Alcohols


ID: J48-Y2005-2630