Asymmetric Guerbet Reaction to Access Chiral Alcohols
Kun Wang, Lin Zhang, Weijun Tang, Huaming Sun, Dong Xue, Ming Lei, Jianliang Xiao, Chao Wang
Abstract
Abstract The first example of an asymmetric Guerbet reaction has been developed. Using commercially available, classic Noyori Ru II ‐diamine‐diphosphine catalysts, well‐known in asymmetric hydrogenation, racemic secondary alcohols are shown to couple with primary alcohols in the presence of a base, affording new chiral alcohols with enantiomeric ratios of up to 99:1. Requiring no reducing agents, the protocol provides an easy, alternative route for the synthesis of chiral alcohols. Mechanistic studies reveal that the reaction proceeds via a Ru‐catalyzed asymmetric hydrogen autotransfer process in concert with a base‐promoted allylic alcohol isomerization.