Rhodium(I)-catalyzed enantioselective hydrogenation of substituted acrylic acids with sterically similar β,β-diaryls

Yang Li; Kaiwu Dong; Zheng Wang; Kuiling Ding

doi:10.1002/anie.201302349

Rhodium(I)-catalyzed enantioselective hydrogenation of substituted acrylic acids with sterically similar β,β-diaryls

Yang Li
, Kaiwu Dong
, Zheng Wang
, Kuiling Ding^*

^*Corresponding author for this work

CAS - Shanghai Institute of Organic Chemistry

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

65 Scopus citations

Abstract

Distinct differentiation: β,β-Disubstituted acrylic acids with sterically similar geminal diaryl groups can be hydrogenated with excellent enantioselectivities in the presence of a Rh^I complex formed in situ with two-component ligands, a chiral secondary phosphine oxide (SPO) and an achiral phosphine (Ph₃P). The sense of asymmetric induction was found to be controlled by the substrate configuration, thus allowing access to both enantiomers of the product with the same catalyst.

Original language	English
Pages (from-to)	6748-6752
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	26
DOIs	https://doi.org/10.1002/anie.201302349
State	Published - 24 Jun 2013
Externally published	Yes

Keywords

asymmetric catalysis
combinatorial chemistry
hydrogenation
rhodium
secondary phosphine oxides

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title = "Rhodium(I)-catalyzed enantioselective hydrogenation of substituted acrylic acids with sterically similar β,β-diaryls",

abstract = "Distinct differentiation: β,β-Disubstituted acrylic acids with sterically similar geminal diaryl groups can be hydrogenated with excellent enantioselectivities in the presence of a RhI complex formed in situ with two-component ligands, a chiral secondary phosphine oxide (SPO) and an achiral phosphine (Ph3P). The sense of asymmetric induction was found to be controlled by the substrate configuration, thus allowing access to both enantiomers of the product with the same catalyst.",

keywords = "asymmetric catalysis, combinatorial chemistry, hydrogenation, rhodium, secondary phosphine oxides",

author = "Yang Li and Kaiwu Dong and Zheng Wang and Kuiling Ding",

year = "2013",

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doi = "10.1002/anie.201302349",

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T1 - Rhodium(I)-catalyzed enantioselective hydrogenation of substituted acrylic acids with sterically similar β,β-diaryls

AU - Li, Yang

AU - Dong, Kaiwu

AU - Wang, Zheng

AU - Ding, Kuiling

PY - 2013/6/24

Y1 - 2013/6/24

N2 - Distinct differentiation: β,β-Disubstituted acrylic acids with sterically similar geminal diaryl groups can be hydrogenated with excellent enantioselectivities in the presence of a RhI complex formed in situ with two-component ligands, a chiral secondary phosphine oxide (SPO) and an achiral phosphine (Ph3P). The sense of asymmetric induction was found to be controlled by the substrate configuration, thus allowing access to both enantiomers of the product with the same catalyst.

AB - Distinct differentiation: β,β-Disubstituted acrylic acids with sterically similar geminal diaryl groups can be hydrogenated with excellent enantioselectivities in the presence of a RhI complex formed in situ with two-component ligands, a chiral secondary phosphine oxide (SPO) and an achiral phosphine (Ph3P). The sense of asymmetric induction was found to be controlled by the substrate configuration, thus allowing access to both enantiomers of the product with the same catalyst.

KW - asymmetric catalysis

KW - combinatorial chemistry

KW - hydrogenation

KW - rhodium

KW - secondary phosphine oxides

UR - https://www.scopus.com/pages/publications/84879365489

U2 - 10.1002/anie.201302349

DO - 10.1002/anie.201302349

M3 - 文章

C2 - 23681837

AN - SCOPUS:84879365489

SN - 1433-7851

VL - 52

SP - 6748

EP - 6752

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 26

ER -

Rhodium(I)-catalyzed enantioselective hydrogenation of substituted acrylic acids with sterically similar β,β-diaryls

Abstract

Keywords

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