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*

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

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

DOI: 10.1021/jo020691c

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Abstract

A complex of 18-crown-6 and KF is effective as a soluble fluoride source to activate asymmetric Sakurai-Hosomi allylations and asymmetric Mukaiyama-type aldol reactions using BINAP and silver(I) triflate as catalyst. Allylations and aldol reactions give products in high yields and remarkable enantioselectivities.

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Silver-Catalyzed Asymmetric Sakurai-Hosomi Allylation of Ketones

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

Scope and Limitations of Chiral B-[3,5-Bis(trifluoromethyl)phenyl]oxazaborilidine Catalyst for Use in the Mukaiyama Aldol Reaction

K. Ishihara, S. Kondo, H. Yamamoto, J. Org. Chem., 2000, 65, 9125-9128.

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Key Words

Hosomi-Sakurai Reaction, Mukaiyama Aldol Addition

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ID: J42-Y2003-560