Chiral Bicylic Guanidine-Catalyzed Conjugate Addition of α-Fluoro-β-Ketoesters to Cyclic Enones

Zhenzhong Jing, Jin Liu, Kek Foo Chin, Wenchao Chen, Choon-Hong Tan and Zhiyong Jiang

Australian Journal of Chemistry, 2014, 67, 1119 – 1123.

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).

Paper download: http://www.publish.csiro.au/CH/CH14187