Efficient and highly enantioselective construction of trifluoromethylated quaternary stereogenic centers via high-pressure mediated organocatalytic conjugate addition of nitromethane to β,β-disubstituted enones

Org Lett. 2014 Nov 21;16(22):5930-3. doi: 10.1021/ol502941d. Epub 2014 Nov 12.

Abstract

A very effective high-pressure-induced acceleration of asymmetric organocatalytic conjugate addition of nitromethane to sterically congested β,β-disubstituted β-CF3 enones has been developed. A combination of pressure (8-10 kbar) and noncovalent catalysis with low-loading of chiral tertiary amine-thioureas (0.5-3 mol %) is shown to provide very efficient access to a wide range of γ-nitroketones containing trifluoromethylated all-carbon quaternary stereogenic centers in the β-position (80-97%, 92-98% ee).

Publication types

  • Research Support, Non-U.S. Gov't