Rh(I)-catalyzed enantioselective hydrogenation of α-substituted ethenylphosphonic acids

Kaiwu Dong; Zheng Wang; Kuiling Ding

doi:10.1021/ja305780z

Rh(I)-catalyzed enantioselective hydrogenation of α-substituted ethenylphosphonic acids

Kaiwu Dong, Zheng Wang, Kuiling Ding

CAS - Shanghai Institute of Organic Chemistry

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

79 Scopus citations

Abstract

A class of chiral Rh(I) catalysts containing monodentate phosphorous acid diesters tautomerized from the corresponding secondary phosphine oxides was discovered by serendipitous hydrolysis of phosphoramidite ligands. The evolved catalysts demonstrated unprecedented enantioselectivities (98-99% ee) and high catalytic activities (as low as 0.01 mol% catalyst loading) in asymmetric hydrogenations of a wide variety of α-aryl-/alkyl-substituted ethenylphosphonic acids, providing a facile approach to the corresponding enantiopure phosphonic acids with significant biological importance.

Original language	English
Pages (from-to)	12474-12477
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	30
DOIs	https://doi.org/10.1021/ja305780z
State	Published - 1 Aug 2012
Externally published	Yes

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title = "Rh(I)-catalyzed enantioselective hydrogenation of α-substituted ethenylphosphonic acids",

abstract = "A class of chiral Rh(I) catalysts containing monodentate phosphorous acid diesters tautomerized from the corresponding secondary phosphine oxides was discovered by serendipitous hydrolysis of phosphoramidite ligands. The evolved catalysts demonstrated unprecedented enantioselectivities (98-99\% ee) and high catalytic activities (as low as 0.01 mol\% catalyst loading) in asymmetric hydrogenations of a wide variety of α-aryl-/alkyl-substituted ethenylphosphonic acids, providing a facile approach to the corresponding enantiopure phosphonic acids with significant biological importance.",

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

year = "2012",

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T1 - Rh(I)-catalyzed enantioselective hydrogenation of α-substituted ethenylphosphonic acids

AU - Dong, Kaiwu

AU - Wang, Zheng

AU - Ding, Kuiling

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Y1 - 2012/8/1

N2 - A class of chiral Rh(I) catalysts containing monodentate phosphorous acid diesters tautomerized from the corresponding secondary phosphine oxides was discovered by serendipitous hydrolysis of phosphoramidite ligands. The evolved catalysts demonstrated unprecedented enantioselectivities (98-99% ee) and high catalytic activities (as low as 0.01 mol% catalyst loading) in asymmetric hydrogenations of a wide variety of α-aryl-/alkyl-substituted ethenylphosphonic acids, providing a facile approach to the corresponding enantiopure phosphonic acids with significant biological importance.

AB - A class of chiral Rh(I) catalysts containing monodentate phosphorous acid diesters tautomerized from the corresponding secondary phosphine oxides was discovered by serendipitous hydrolysis of phosphoramidite ligands. The evolved catalysts demonstrated unprecedented enantioselectivities (98-99% ee) and high catalytic activities (as low as 0.01 mol% catalyst loading) in asymmetric hydrogenations of a wide variety of α-aryl-/alkyl-substituted ethenylphosphonic acids, providing a facile approach to the corresponding enantiopure phosphonic acids with significant biological importance.

UR - https://www.scopus.com/pages/publications/84864468533

U2 - 10.1021/ja305780z

DO - 10.1021/ja305780z

M3 - 文章

C2 - 22783876

AN - SCOPUS:84864468533

SN - 0002-7863

VL - 134

SP - 12474

EP - 12477

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 30

ER -

Rh(I)-catalyzed enantioselective hydrogenation of α-substituted ethenylphosphonic acids

Abstract

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