Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N-Heterocyclic Carbene Catalyst

作者:Jang Ki Po; Hutson Gerri E; Johnston Ryne C; McCusker Elizabeth O; Cheong Paul H Y*; Scheidt Karl A
来源:Journal of the American Chemical Society, 2014, 136(1): 76-79.
DOI:10.1021/ja410932t

摘要

A highly selective NHC-catalyzed synthesis of gamma-butyrolactones from the fusion of enals and alpha-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C-1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.