Asymmetric Morita−Baylis−Hillman Reactions Catalyzed by Chiral Brønsted Acids

作者：Nolan T. McDougal, Scott E. Schaus · 发表于：Journal of the American Chemical Society · 年份：2003 · DOI：10.1021/ja037705w · 被引用次数：304 · 研究领域：Asymmetric Synthesis and Catalysis、Asymmetric Hydrogenation and Catalysis、Chemical Synthesis and Analysis

Chiral BINOL-derived Brønsted acids catalyze the enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2-20 mol % of the chiral Brønsted acid 2e or 2f and triethylphosphine as the nucleophilic promoter. The reaction products are obtained in good yields (39-88%) and high enantioselectivities (67-96% ee). The Brønsted-acid-catalyzed reaction is the first example of a highly enantioselective asymmetric MBH reaction of cyclohexenone with aldehydes.