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Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study.

Research paper by Zhiping Z Zeng, Ping P Luo, Yao Y Jiang, Yan Y Liu, Guo G Tang, Pengxiang P Xu, Yufen Y Zhao, G Michael GM Blackburn

Indexed on: 25 Aug '11Published on: 25 Aug '11Published in: Organic & Biomolecular Chemistry



Abstract

A novel pyrrolidine-based chiral phosphoproline is an effective bifunctional organocatalyst for the asymmetric Michael addition of ketones to nitroolefins giving high levels of diastereo- and enantio-selectivities (up to > 99 : 1 dr and 96% ee). anti-SR Transition state has the lowest barrier which controls the stereoselectivity, in agreement with experimental results.