Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation

Xiao Hui Yang; Ke Wang; Shou Fei Zhu; Jian Hua Xie; Qi Lin Zhou

doi:10.1021/ja510990v

Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation

Xiao Hui Yang, Ke Wang, Shou Fei Zhu, Jian Hua Xie^*, Qi Lin Zhou

^*Corresponding author for this work

Nankai University

Research output: Contribution to journal › Article › peer-review

67 Citations (Scopus)

Abstract

A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities even at extremely low catalyst loading (0.001 mol %).

Original language	English
Pages (from-to)	17426-17429
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	50
DOIs	https://doi.org/10.1021/ja510990v
Publication status	Published - 17 Dec 2014
Externally published	Yes

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abstract = "A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities even at extremely low catalyst loading (0.001 mol %).",

author = "Yang, {Xiao Hui} and Ke Wang and Zhu, {Shou Fei} and Xie, {Jian Hua} and Zhou, {Qi Lin}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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doi = "10.1021/ja510990v",

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AU - Yang, Xiao Hui

AU - Wang, Ke

AU - Zhu, Shou Fei

AU - Xie, Jian Hua

AU - Zhou, Qi Lin

PY - 2014/12/17

Y1 - 2014/12/17

N2 - A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities even at extremely low catalyst loading (0.001 mol %).

AB - A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities even at extremely low catalyst loading (0.001 mol %).

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DO - 10.1021/ja510990v

M3 - Article

C2 - 25437900

AN - SCOPUS:84919384159

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SP - 17426

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 50

ER -

Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation

Abstract

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