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Asymmetric Michael Addition of N-tert-Butanesulfinyl Imidate with α,β-Unsaturated Diesters: Scope and Application to the Synthesis of Indanone Derivatives

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journal contribution
posted on 05.04.2013 by Jinfang Wang, Yu Zhou, Lei Zhang, Zeng Li, Xianjie Chen, Hong Liu
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.