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

摘要

A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states was employed to guide a rational design strategy and achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl saturated imidazolium-derived NHC catalyst. This new annulation is compatible with a wide range of acyl phosphonates and α,β-unsaturated aldehydes.