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 (free Supporting Information)
see article for more reactions
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.
see article for more examples