Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

Xiao Hui Yang; Hai Tao Yue; Na Yu; Yi Pan Li; Jian Hua Xie; Qi Lin Zhou

doi:10.1039/c6sc04609f

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

Xiao Hui Yang, Hai Tao Yue, Na Yu, Yi Pan Li, Jian Hua Xie^*, Qi Lin Zhou

^*Corresponding author for this work

Nankai University

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

37 Citations (Scopus)

Abstract

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

Original language	English
Pages (from-to)	1811-1814
Number of pages	4
Journal	Chemical Science
Volume	8
Issue number	3
DOIs	https://doi.org/10.1039/c6sc04609f
Publication status	Published - 2017
Externally published	Yes

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title = "Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols",

abstract = "We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.",

author = "Yang, {Xiao Hui} and Yue, {Hai Tao} and Na Yu and Li, {Yi Pan} and Xie, {Jian Hua} and Zhou, {Qi Lin}",

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T1 - Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

AU - Yang, Xiao Hui

AU - Yue, Hai Tao

AU - Yu, Na

AU - Li, Yi Pan

AU - Xie, Jian Hua

AU - Zhou, Qi Lin

PY - 2017

Y1 - 2017

N2 - We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

AB - We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

UR - http://www.scopus.com/inward/record.url?scp=85014100490&partnerID=8YFLogxK

U2 - 10.1039/c6sc04609f

DO - 10.1039/c6sc04609f

M3 - Article

AN - SCOPUS:85014100490

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VL - 8

SP - 1811

EP - 1814

JO - Chemical Science

JF - Chemical Science

IS - 3

ER -

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

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