Organocatalytic enantioselective sulfa-Michael addition of thiocarboxylic acids to β-trifluoromethyl-α,β-unsaturated ketones for the construction of stereogenic carbon center bearing a sulfur atom and a trifluoromethyl group

Add time:08/03/2019    Source:sciencedirect.com

An organocatalyzed asymmetric sulfa-Michael addition of thiocarboxylic acids to β-trifluoromethyl-α,β-unsaturated ketones with a chiral bifunctional amine-squaramide as the catalyst is presented. A wide range of chiral ketone compounds bearing a sulfur atom and a trifluoromethyl group at the stereogenic carbon center could be obtained with excellent results (up to 99% yield, 97% ee) under mild conditions. The developed catalytic system is well-tolerated to both (E)-and (Z)-β-trifluoromethylated-α,β-unsaturated ketones.

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