Asymmetric Guerbet Reaction to Access Chiral Alcohols



Wang, Kun, Zhang, Lin, Tang, Weijun, Sun, Huaming, Xue, Dong, Lei, Ming, Xiao, Jianliang ORCID: 0000-0003-2010-247X and Wang, Chao
(2020) Asymmetric Guerbet Reaction to Access Chiral Alcohols. Angewandte Chemie International Edition, 59 (28). pp. 11408-11415.

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Abstract

The first example of an asymmetric Guerbet reaction has been developed. Using commercially available, classic Noyori RuII -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.

Item Type: Article
Uncontrolled Keywords: alkylation, asymmetric catalysis, chiral alcohol, hydrogen autotransfer, ruthenium
Depositing User: Symplectic Admin
Date Deposited: 01 Oct 2020 08:57
Last Modified: 18 Jan 2023 23:30
DOI: 10.1002/ange.202003104
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3103150