N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides

Hao Guo; Fen Xing; Guang-Fen Du; Kuo-Wei Huang; Bin Dai; Lin He

doi:10.1021/acs.joc.5b01845

N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides

Hao Guo, Fen Xing, Guang-Fen Du, Kuo-Wei Huang, Bin Dai, Lin He

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

29 Scopus citations

Abstract

An efficient N-heterocyclic carbene (NHC)-catalysed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol% of the NHC catalyst, both γ-alkyl and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Brønsted base to promote the conjugate addition.

Original language	English (US)
Pages (from-to)	12606-12613
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	80
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.5b01845
State	Published - Nov 30 2015

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KAUST Repository Item: Exported on 2020-10-01

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10.1021/acs.joc.5b01845

https://repository.kaust.edu.sa/bitstream/10754/582931/1/acs2Ejoc2E5b01845.pdf

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title = "N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides",

abstract = "An efficient N-heterocyclic carbene (NHC)-catalysed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol% of the NHC catalyst, both γ-alkyl and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Br{\o}nsted base to promote the conjugate addition.",

author = "Hao Guo and Fen Xing and Guang-Fen Du and Kuo-Wei Huang and Bin Dai and Lin He",

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language = "English (US)",

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T1 - N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides

AU - Guo, Hao

AU - Xing, Fen

AU - Du, Guang-Fen

AU - Huang, Kuo-Wei

AU - Dai, Bin

AU - He, Lin

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2015/11/30

Y1 - 2015/11/30

N2 - An efficient N-heterocyclic carbene (NHC)-catalysed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol% of the NHC catalyst, both γ-alkyl and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Brønsted base to promote the conjugate addition.

AB - An efficient N-heterocyclic carbene (NHC)-catalysed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol% of the NHC catalyst, both γ-alkyl and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Brønsted base to promote the conjugate addition.

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U2 - 10.1021/acs.joc.5b01845

DO - 10.1021/acs.joc.5b01845

M3 - Article

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EP - 12613

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 24

ER -

N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides

Abstract

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CCDC 1433704: Experimental Crystal Structure Determination : 5-(3-(4-chlorophenyl)-3-oxo-1-phenylpropyl)-5-methylfuran-2(5H)-one

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N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides

Abstract

Bibliographical note

Access to Document

Other files and links

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Datasets

CCDC 1433704: Experimental Crystal Structure Determination : 5-(3-(4-chlorophenyl)-3-oxo-1-phenylpropyl)-5-methylfuran-2(5H)-one

Cite this