Kinetic resolution of hindered Morita-Baylis-Hillman adducts by Rh(I)-catalyzed asymmetric 1,4-addition/β-hydroxyelimination

Yazhou Wang; Xiangqing Feng; Haifeng Du

doi:10.1021/ol202069e

Kinetic resolution of hindered Morita-Baylis-Hillman adducts by Rh(I)-catalyzed asymmetric 1,4-addition/β-hydroxyelimination

Org Lett. 2011 Sep 16;13(18):4954-7. doi: 10.1021/ol202069e. Epub 2011 Aug 15.

Authors

Yazhou Wang¹, Xiangqing Feng, Haifeng Du

Affiliation

¹ Beijing National Laboratory of Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

PMID: 21842895
DOI: 10.1021/ol202069e

Abstract

A kinetic resolution of hindered Morita-Baylis-Hillman adducts has been successfully achieved in excellent selectivities via Rh(I)-catalyzed asymmetric 1,4-addition/β-hydroxyelimination with the use of a chiral sulfinamide/olefin hybrid ligand. This study provides a novel and efficient access to both optically active hindered highly functionalized alkenes and Morita-Baylis-Hillman adducts.