Asymmetric Hydrogenation of Pyridinium Salts with an Iridium Phosphole Catalyst

Abstract

Iridium-catalyzed asymmetric hydrogenation of N-alkyl-2-alkylpyridinium salts provided 2-aryl-substituted piperidines with high levels of enantioselectivity. Simple benzyl and other alkyl groups successfully activated the challenging pyridine substrates toward hydrogenation. The use of the unusual chiral-phosphole-based MP(2) -SEGPHOS was the key to the success of this approach which provides a versatile and practical procedure for the synthesis of chiral piperidines.