Enantio‐ and Diastereoselective Hydrogenation of Farnesol and O‐Protected Derivatives: Stereocontrol by Changing the CC Bond Configuration

Abstract

Four isomers–one catalyst: The four stereoisomers of hexahydrofarnesol can be prepared with high enantio- and diastereoselectivity by using the same chiral iridium catalyst 1 with different cis/trans isomers of farnesol (see scheme; BArF=tetrakis[bis-3,5-(trifluoromethyl)phenyl]borate). Both the internal trialkyl-substituted CC bond and the allylic alcohol unit are hydrogenated with high facial selectivity.