Université de Reims Champagne Ardenne, CNRS, Institut de Chimie Moléculaire de Reims UMR 7312, 51097 Reims, France.
Chem Commun (Camb). 2020 Jun 18;56(49):6640-6643. doi: 10.1039/d0cc02058c.
The asymmetric allylic alkylation (AAA) of α-aryl γ-lactones involving the activation of Morita-Baylis-Hillman (MBH) carbonates by an original chiral Lewis base is reported. A wide range of γ-lactones bearing a quaternary stereocentre was thus obtained in both high yields and high enantiomeric ratios. The direct alkylation by MBH alcohol using in situ activation has been also established. Additionally synthetically useful functional transformations of groups surrounding the quaternary stereocentre have been performed.
本文报道了通过一种原创手性路易斯碱对 Morita-Baylis-Hillman（MBH）碳酸酯的活化，实现α-芳基γ-内酯的不对称烯丙基烷基化（AAA）反应。通过该方法，可以高收率和高对映选择性地得到一系列含有季立体中心的γ-内酯。此外，本文还建立了通过原位活化的 MBH 醇的直接烷基化反应。同时，围绕季立体中心的官能团的一些具有合成用途的转化也被实现。
