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Org Biomol Chem. 2016 Jan 14;14(2):752-760. doi: 10.1039/c5ob01958c.

Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction.

Organic & biomolecular chemistry

Haiwen Hu, Shuxian Yu, Linglong Zhu, Lingxiu Zhou, Weihui Zhong

Affiliations

  1. Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, PR China. [email protected].

PMID: 26584209 DOI: 10.1039/c5ob01958c

Abstract

A series of air-stable ferrocenylphosphines LB1-LB8 were designed and prepared in high yields. (R,SFc)-ferrocenylphosphine LB5 was found to efficiently promote the asymmetric [3 + 2] cycloaddition of Morita-Baylis-Hillman carbonates with maleimides to afford the corresponding bicyclic imides with 84-99% ee and 67-99% yield. Interestingly, the configuration of these products was contrary to those reported in the literature.

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