Direct Enantio- and Diastereoselective Zn-ProPhenol-Catalyzed Mannich Reactions of CF3 - and SCF3 -Substituted Ketones

Organic Letters
Barry M TrostElumalai Gnanamani

Abstract

Enantioselective incorporation of trifluoromethyl (-CF3) and trifuoromethylthio (-SCF3) groups in small molecules is of high interest to modulate the potency and pharmacological properties of drug candidates. Herein, we report a Zn-ProPhenol catalyzed diastereo- and enantioselective Mannich addition of α-trifluoromethyl- and α-trifuoromethylthio-substituted ketones. This transformation uses cyclic and acyclic ketones and generates quaternary trifluoromethyl and tetrasubstituted trifuoromethylthio stereogenic centers in excellent yields and selectivities.

References

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