Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams: Preparation of Chiral 4-Aryl-2-Pyrrolidones

Jo Hsuan Fang; Chiung An Chang; Balraj Gopula; Ting Shen Kuo; Ping Yu Wu; Julian P. Henschke; Hsyueh Liang Wu

doi:10.1002/ajoc.201600032

Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams: Preparation of Chiral 4-Aryl-2-Pyrrolidones

Jo Hsuan Fang, Chiung An Chang, Balraj Gopula, Ting Shen Kuo, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

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

16 Scopus citations

Abstract

The preparation of chiral 4-aryl-2-pyrrolidones by conjugate addition catalyzed by a rhodium(I) complex, comprising the chiral bicyclo[2.2.1] diene ligand 1e, is reported. The reaction of various arylboronic acids and α,β-unsaturated γ-lactams 2 bearing various N-substituents proceeds in a highly stereoselective fashion (93-99.5% ee) even in the presence of only 0.5mol% of the Rh catalyst affording the corresponding addition products in 31-99% yield.

Original language	English
Pages (from-to)	481-485
Number of pages	5
Journal	Asian Journal of Organic Chemistry
Volume	5
Issue number	4
DOIs	https://doi.org/10.1002/ajoc.201600032
State	Published - 1 Apr 2016
Externally published	Yes

Keywords

4-aryl-2-pyrrolidones
Arylboronic acids
Conjugate addition
Homogeneous catalysis
Rhodium

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10.1002/ajoc.201600032

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title = "Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams: Preparation of Chiral 4-Aryl-2-Pyrrolidones",

abstract = "The preparation of chiral 4-aryl-2-pyrrolidones by conjugate addition catalyzed by a rhodium(I) complex, comprising the chiral bicyclo[2.2.1] diene ligand 1e, is reported. The reaction of various arylboronic acids and α,β-unsaturated γ-lactams 2 bearing various N-substituents proceeds in a highly stereoselective fashion (93-99.5% ee) even in the presence of only 0.5mol% of the Rh catalyst affording the corresponding addition products in 31-99% yield.",

keywords = "4-aryl-2-pyrrolidones, Arylboronic acids, Conjugate addition, Homogeneous catalysis, Rhodium",

author = "Fang, {Jo Hsuan} and Chang, {Chiung An} and Balraj Gopula and Kuo, {Ting Shen} and Wu, {Ping Yu} and Henschke, {Julian P.} and Wu, {Hsyueh Liang}",

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year = "2016",

month = apr,

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doi = "10.1002/ajoc.201600032",

language = "English",

volume = "5",

pages = "481--485",

journal = "Asian Journal of Organic Chemistry",

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T1 - Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams

T2 - Preparation of Chiral 4-Aryl-2-Pyrrolidones

AU - Fang, Jo Hsuan

AU - Chang, Chiung An

AU - Gopula, Balraj

AU - Kuo, Ting Shen

AU - Wu, Ping Yu

AU - Henschke, Julian P.

AU - Wu, Hsyueh Liang

PY - 2016/4/1

Y1 - 2016/4/1

N2 - The preparation of chiral 4-aryl-2-pyrrolidones by conjugate addition catalyzed by a rhodium(I) complex, comprising the chiral bicyclo[2.2.1] diene ligand 1e, is reported. The reaction of various arylboronic acids and α,β-unsaturated γ-lactams 2 bearing various N-substituents proceeds in a highly stereoselective fashion (93-99.5% ee) even in the presence of only 0.5mol% of the Rh catalyst affording the corresponding addition products in 31-99% yield.

AB - The preparation of chiral 4-aryl-2-pyrrolidones by conjugate addition catalyzed by a rhodium(I) complex, comprising the chiral bicyclo[2.2.1] diene ligand 1e, is reported. The reaction of various arylboronic acids and α,β-unsaturated γ-lactams 2 bearing various N-substituents proceeds in a highly stereoselective fashion (93-99.5% ee) even in the presence of only 0.5mol% of the Rh catalyst affording the corresponding addition products in 31-99% yield.

KW - 4-aryl-2-pyrrolidones

KW - Arylboronic acids

KW - Conjugate addition

KW - Homogeneous catalysis

KW - Rhodium

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U2 - 10.1002/ajoc.201600032

DO - 10.1002/ajoc.201600032

M3 - Article

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SN - 2193-5807

VL - 5

SP - 481

EP - 485

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 4

ER -

Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams: Preparation of Chiral 4-Aryl-2-Pyrrolidones

Abstract

Keywords

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