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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).

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