Asymmetric Alkyl-Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins

N A Owston; G C Fu

doi:10.1021/ja105924f

Asymmetric Alkyl-Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins

N A Owston, G C Fu

The University of Manchester

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

Abstract

A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with allylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.

Original language	English
Pages (from-to)	11908-11909
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	132
Issue number	34
DOIs	https://doi.org/10.1021/ja105924f
Publication status	Published - 2010

Keywords

c-f bonds
alpha-bromoketones
grignard-reagents
arylzinc reagents
halides
activation
chlorides

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10.1021/ja105924f

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title = "Asymmetric Alkyl-Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins",

abstract = "A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with allylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.",

keywords = "c-f bonds, alpha-bromoketones, grignard-reagents, arylzinc reagents, halides, activation, chlorides",

author = "Owston, {N A} and Fu, {G C}",

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journal = "Journal of the American Chemical Society",

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AU - Owston, N A

AU - Fu, G C

N1 - 643LA Times Cited:66 Cited References Count:21

PY - 2010

Y1 - 2010

N2 - A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with allylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.

AB - A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with allylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.

KW - c-f bonds

KW - alpha-bromoketones

KW - grignard-reagents

KW - arylzinc reagents

KW - halides

KW - activation

KW - chlorides

U2 - 10.1021/ja105924f

DO - 10.1021/ja105924f

M3 - Article

SN - 1520-5126

VL - 132

SP - 11908

EP - 11909

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 34

ER -

Asymmetric Alkyl-Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins

Abstract

Keywords

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