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.

Text
K Wang Manuscript accepted.pdf - Author Accepted Manuscript
Download (1MB) | Preview

Official URL: http://dx.doi.org/10.1002/anie.202003104

Abstract

The first example of an asymmetric Guerbet reaction has been developed. Using commercially available, classic Noyori Ru<sup>II</sup> -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:	20 Jan 2024 13:39
DOI:	10.1002/ange.202003104
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3103150