Catalytic asymmetric [2,3]-sigmatropic rearrangement of sulfur ylides generated from copper(I) carbenoids and allyl sulfides

Xiaomei Zhang; Zhaohui Qu; Zhihua Ma; Weifeng Shi; Xianglin Jin; Jianbo Wang

doi:10.1021/jo025687f

Catalytic asymmetric [2,3]-sigmatropic rearrangement of sulfur ylides generated from copper(I) carbenoids and allyl sulfides

J Org Chem. 2002 Aug 9;67(16):5621-5. doi: 10.1021/jo025687f.

Authors

Xiaomei Zhang¹, Zhaohui Qu, Zhihua Ma, Weifeng Shi, Xianglin Jin, Jianbo Wang

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry, Peking University, Beijing 100871, P. R. China.

PMID: 12153260
DOI: 10.1021/jo025687f

Abstract

Catalytic asymmetric sulfur ylide [2,3]-sigmatropic rearrangement of carbenoids generated from aryldiazoacetates has been investigated with a number of chiral Rh(II) and Cu(I) catalysts, and moderately high enantioselectivity (52-78% ee) can be achieved with Cu(MeCN)(4)PF(6)/2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline].