Highly enantioselective [3+2] cycloadditions of terminal allenoates with β-trifluoromethyl α,β-enones

Abstract

Highly enantio- and diastereoselective phosphine-catalyzed [3+2] cycloadditions of terminal allenoates with β-perfluoroalkyl α,β-enones leading to a range of trifluoromethylated cyclopentenes with two contiguous chiral centers (up to 99% yield with 99% ee) have been developed. Moreover, these reactions could be performed at the gram scale by using only 1 mol% catalyst. The method developed here was also applied to the concise synthesis of trifluoromethylated DGAT-1 inhibitor.