Highly Stereoselective C-C Bond Formation by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor Carbenoids and Chiral Allylic Alcohols

Zhanjie Li, Brendan T. Parr and Huw M. L. Davies*

*Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States, Email: hmdavieemory.edu

Z. Li, B. T. Parr, H. M. L. Davies, J. Am. Chem. Soc., 2012, 134, 10942-10946.

DOI: 10.1021/ja303023n

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Abstract

The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium carbenoids and chiral allyl alcohols generates two vicinal stereogenic centers in a convergent C-C bond forming process. Any of the four possible stereoisomers can be selectively synthesized by appropriate combination of the chiral catalyst Rh₂(DOSP)₄ and the chiral alcohol.

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Key Words

Allylations, α-hydroxy carboxylic derivatives

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ID: J48-Y2012-2130