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

68 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

Access to Document

10.1021/ja510990v

Cite this

@article{0a91ed613dc44ea08ea40e949828fa38,

title = "Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation",

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.",

year = "2014",

month = dec,

day = "17",

doi = "10.1021/ja510990v",

language = "English",

volume = "136",

pages = "17426--17429",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "50",

}

TY - JOUR

T1 - Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation

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 %).

UR - https://www.scopus.com/pages/publications/84919384159

U2 - 10.1021/ja510990v

DO - 10.1021/ja510990v

M3 - Article

C2 - 25437900

AN - SCOPUS:84919384159

SN - 0002-7863

VL - 136

SP - 17426

EP - 17429

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

Access to Document

Other files and links

Fingerprint

Cite this