Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate
Addition Reactions of alpha-Functionalized alpha,beta-Unsaturated
Carbonyl Substrates

Jian-Bo Xie; Siqi Lin; Shuo Qiao; Guigen Li

Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate Addition Reactions of alpha-Functionalized alpha,beta-Unsaturated Carbonyl Substrates

Jian-Bo Xie, Siqi Lin, Shuo Qiao, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article

Abstract

An efficient catalytic system has been established for the asymmetric boron conjugate addition of B(2)pin(2) onto alpha-functionalized (involving C, N, O, and Cl) a alpha,beta-unsaturated carbonyls under mild, neutral conditions involving Cu[(S)-(R)-ppfa]Cl, AgNTf2, and alcohols. The dual additives of AgNTf2 and alcohols were found to play crucial roles for achieving high catalytic activity and enantio- and diastereoselectivity (up to 98% ee and 70:1 dr).

Original language	English
Pages (from-to)	3926-3929
Journal	Organic Letters
State	Published - Aug 2016

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@article{c8970370bda64f75b7d17b286505fe3b,

title = "Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate Addition Reactions of alpha-Functionalized alpha,beta-Unsaturated Carbonyl Substrates",

abstract = "An efficient catalytic system has been established for the asymmetric boron conjugate addition of B(2)pin(2) onto alpha-functionalized (involving C, N, O, and Cl) a alpha,beta-unsaturated carbonyls under mild, neutral conditions involving Cu[(S)-(R)-ppfa]Cl, AgNTf2, and alcohols. The dual additives of AgNTf2 and alcohols were found to play crucial roles for achieving high catalytic activity and enantio- and diastereoselectivity (up to 98% ee and 70:1 dr).",

author = "Jian-Bo Xie and Siqi Lin and Shuo Qiao and Guigen Li",

year = "2016",

month = aug,

language = "English",

pages = "3926--3929",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

}

TY - JOUR

T1 - Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate Addition Reactions of alpha-Functionalized alpha,beta-Unsaturated Carbonyl Substrates

AU - Xie, Jian-Bo

AU - Lin, Siqi

AU - Qiao, Shuo

AU - Li, Guigen

PY - 2016/8

Y1 - 2016/8

N2 - An efficient catalytic system has been established for the asymmetric boron conjugate addition of B(2)pin(2) onto alpha-functionalized (involving C, N, O, and Cl) a alpha,beta-unsaturated carbonyls under mild, neutral conditions involving Cu[(S)-(R)-ppfa]Cl, AgNTf2, and alcohols. The dual additives of AgNTf2 and alcohols were found to play crucial roles for achieving high catalytic activity and enantio- and diastereoselectivity (up to 98% ee and 70:1 dr).

AB - An efficient catalytic system has been established for the asymmetric boron conjugate addition of B(2)pin(2) onto alpha-functionalized (involving C, N, O, and Cl) a alpha,beta-unsaturated carbonyls under mild, neutral conditions involving Cu[(S)-(R)-ppfa]Cl, AgNTf2, and alcohols. The dual additives of AgNTf2 and alcohols were found to play crucial roles for achieving high catalytic activity and enantio- and diastereoselectivity (up to 98% ee and 70:1 dr).

M3 - Article

SP - 3926

EP - 3929

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -

Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate Addition Reactions of alpha-Functionalized alpha,beta-Unsaturated Carbonyl Substrates

Abstract

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