Diastereoselective Aldol Reaction of α‐Azido Ketones with α‐CF3 Pyruvate to Organoazides with Vicinal Tetrasubstituted Carbons

Abstract

A direct diastereoselective aldol reaction of cyclic or acyclic α‐azido ketones with α‐trifluoromethyl (CF3) pyruvate catalysed by DABCO is developed, which allowed the facile access of CF3‐containing multifunctional organoazides with vicinal tetrasubstituted carbons in good to high yields and diastereoselectivities. Moreover, phenylethynyl trifluoro‐ and difluoromethyl ketones are also viable substrates. Up to 50% enantioselectivity could be obtained in the initial exploration of the catalytic asymmetric variant.