Asymmetric Michael Addition of N-tert-Butanesulfinyl Imidate with α,β-Unsaturated Diesters: Scope and Application to the Synthesis of Indanone Derivatives
journal contributionposted on 05.04.2013 by Jinfang Wang, Yu Zhou, Lei Zhang, Zeng Li, Xianjie Chen, Hong Liu
Any type of content formally published in an academic journal, usually following a peer-review process.
An additive-free and highly diastereoselective Michael addition reaction of an N-tert-butanesulfinyl imidate to α,β-unsaturated diesters has been developed using LDA as a base with good to excellent yields. The utility of this chemistry is further demonstrated by the asymmetric synthesis of 3-substituted indanone derivatives 8a, 8d, 8e, and 8i with high enantiomeric excess, which are potential building blocks for preparing biologically active lead compounds.