Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

Chunlin Wu; Guizhou Yue; Christian Duc-Trieu Nielsen; Kai Xu; Hajime Hirao; Jianrong Zhou

doi:10.1021/jacs.5b11441

Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

Chunlin Wu
, Guizhou Yue
, Christian Duc-Trieu Nielsen
, Kai Xu
, Hajime Hirao^*
, Jianrong Zhou^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

79 Citations (Scopus)

Abstract

Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

Original language	English
Pages (from-to)	742-745
Journal	Journal of the American Chemical Society
Volume	138
Issue number	3
DOIs	https://doi.org/10.1021/jacs.5b11441
Publication status	Published - 27 Jan 2016
Externally published	Yes

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title = "Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts",

abstract = "Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.",

author = "Chunlin Wu and Guizhou Yue and Nielsen, \{Christian Duc-Trieu\} and Kai Xu and Hajime Hirao and Jianrong Zhou",

year = "2016",

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doi = "10.1021/jacs.5b11441",

language = "English",

volume = "138",

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journal = "Journal of the American Chemical Society",

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TY - JOUR

T1 - Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

AU - Wu, Chunlin

AU - Yue, Guizhou

AU - Nielsen, Christian Duc-Trieu

AU - Xu, Kai

AU - Hirao, Hajime

AU - Zhou, Jianrong

PY - 2016/1/27

Y1 - 2016/1/27

N2 - Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

AB - Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

UR - https://www.scopus.com/pages/publications/84956825727

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-84956825727&origin=recordpage

U2 - 10.1021/jacs.5b11441

DO - 10.1021/jacs.5b11441

M3 - RGC 21 - Publication in refereed journal

SN - 0002-7863

VL - 138

SP - 742

EP - 745

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 3

ER -

Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

Abstract

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