Asymmetric catalysis of Morita-Baylis-Hillman reactions by chiral phosphine Lewis bases bearing multiple phenol groups

Min Shi; Ying-Hao Liu; Lian-Hui Chen

doi:10.1002/chir.20313

Asymmetric catalysis of Morita-Baylis-Hillman reactions by chiral phosphine Lewis bases bearing multiple phenol groups

Chirality. 2007 Feb;19(2):124-8. doi: 10.1002/chir.20313.

Authors

Min Shi¹, Ying-Hao Liu, Lian-Hui Chen

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China. mshi@mail.sioc.ac.cn

PMID: 17117401
DOI: 10.1002/chir.20313

Abstract

In the Morita-Baylis-Hillman (MBH) reactions of arylaldehydes with methyl vinyl ketone, it was observed that in the presence of a catalytic amount of a chiral phosphine Lewis base (CPLB) bearing multiple phenol groups, such as CPLB1 (10 mol %), the corresponding MBH adducts could be obtained in moderate to good yields with low to moderate ee's (4-45% ee) at ambient temperature (10 degrees C) in THF.