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RESEARCH ARTICLE
Contents Vol 67(7)

Chiral Bicyclic Guanidine-Catalysed Conjugate Addition of α-Fluoro-β-Ketoesters to Cyclic Enones

Zhenzhong Jing A , Jin Liu A , Kek Foo Chin B , Wenchao Chen A , Choon-Hong Tan B and Zhiyong Jiang A C
+ Author Affiliations
- Author Affiliations

A Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004, China.

B Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore.

C Corresponding author. Email: chmjzy@henu.edu.cn

Australian Journal of Chemistry 67(7) 1119-1123 https://doi.org/10.1071/CH14187
Submitted: 29 March 2014  Accepted: 30 April 2014   Published: 23 May 2014

Abstract

By utilising a chiral bicyclic guanidine as catalyst and triethylamine as additive, the first asymmetric Michael addition of α-fluoro-β-ketoesters to various cyclic enones has been successfully developed, affording a variety of Michael adducts with potential synthetic utilities with satisfactory stereoselectivity (up to 94 % ee and 4.3 : 1 dr).


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