Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols

Zhijian Huang; Xuan Huang; Baosheng Li; Chengli Mou; Song Yang; Bao An Song; Yonggui Robin Chi

doi:10.1021/jacs.6b04624

Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols

Zhijian Huang, Xuan Huang, Baosheng Li, Chengli Mou, Song Yang, Bao An Song^*, Yonggui Robin Chi

^*Corresponding author for this work

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

121 Citations (Scopus)

Abstract

A carbene-catalyzed desymmetrization of prochiral bisphenol compounds bearing remote P-stereogenic centers is disclosed. The catalytic reactions can be performed on gram scales with 1 mol % N-heterocyclic carbene (NHC) catalyst, providing efficient access to enantiomerically enriched P-stereogenic phosphinates. The chiral phosphinates prepared with our method can find widespread applications as asymmetric organic catalysts and ligands.

Original language	English
Pages (from-to)	7524-7527
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	24
DOIs	https://doi.org/10.1021/jacs.6b04624
Publication status	Published - Jun 22 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.6b04624

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abstract = "A carbene-catalyzed desymmetrization of prochiral bisphenol compounds bearing remote P-stereogenic centers is disclosed. The catalytic reactions can be performed on gram scales with 1 mol % N-heterocyclic carbene (NHC) catalyst, providing efficient access to enantiomerically enriched P-stereogenic phosphinates. The chiral phosphinates prepared with our method can find widespread applications as asymmetric organic catalysts and ligands.",

author = "Zhijian Huang and Xuan Huang and Baosheng Li and Chengli Mou and Song Yang and Song, {Bao An} and Chi, {Yonggui Robin}",

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T1 - Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols

AU - Huang, Zhijian

AU - Huang, Xuan

AU - Li, Baosheng

AU - Mou, Chengli

AU - Yang, Song

AU - Song, Bao An

AU - Chi, Yonggui Robin

PY - 2016/6/22

Y1 - 2016/6/22

N2 - A carbene-catalyzed desymmetrization of prochiral bisphenol compounds bearing remote P-stereogenic centers is disclosed. The catalytic reactions can be performed on gram scales with 1 mol % N-heterocyclic carbene (NHC) catalyst, providing efficient access to enantiomerically enriched P-stereogenic phosphinates. The chiral phosphinates prepared with our method can find widespread applications as asymmetric organic catalysts and ligands.

AB - A carbene-catalyzed desymmetrization of prochiral bisphenol compounds bearing remote P-stereogenic centers is disclosed. The catalytic reactions can be performed on gram scales with 1 mol % N-heterocyclic carbene (NHC) catalyst, providing efficient access to enantiomerically enriched P-stereogenic phosphinates. The chiral phosphinates prepared with our method can find widespread applications as asymmetric organic catalysts and ligands.

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U2 - 10.1021/jacs.6b04624

DO - 10.1021/jacs.6b04624

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 24

ER -

Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols

Abstract

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ASJC Scopus Subject Areas

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