N-Heterocyclic-Carbene-Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2-(Trimethylsilyloxy)furan and Enones

Ying Wang; Guang Fen Du; Fen Xing; Kuo-Wei Huang; Bin Dai; Lin He

doi:10.1002/ajoc.201500348

N-Heterocyclic-Carbene-Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2-(Trimethylsilyloxy)furan and Enones

Ying Wang, Guang Fen Du, Fen Xing, Kuo-Wei Huang, Bin Dai, Lin He

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

10 Scopus citations

Abstract

N-heterocyclic carbenes have been utilised as highly efficient nucleophilic organocatalysts to mediate vinylogous Mukaiyama/Michael reactions of 2-(trimethylsilyloxy)furan with enones to afford γ-substituted butenolides in 44-99% yield with 3:1-32:1 diastereoselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	1362-1365
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	4
Issue number	12
DOIs	https://doi.org/10.1002/ajoc.201500348
State	Published - Oct 15 2015

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title = "N-Heterocyclic-Carbene-Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2-(Trimethylsilyloxy)furan and Enones",

abstract = "N-heterocyclic carbenes have been utilised as highly efficient nucleophilic organocatalysts to mediate vinylogous Mukaiyama/Michael reactions of 2-(trimethylsilyloxy)furan with enones to afford γ-substituted butenolides in 44-99% yield with 3:1-32:1 diastereoselectivity. {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Ying Wang and Du, {Guang Fen} and Fen Xing and Kuo-Wei Huang and Bin Dai and Lin He",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Shihezi University[2012ZRKXJQ06]",

year = "2015",

month = oct,

day = "15",

doi = "10.1002/ajoc.201500348",

language = "English (US)",

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pages = "1362--1365",

journal = "Asian Journal of Organic Chemistry",

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T1 - N-Heterocyclic-Carbene-Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2-(Trimethylsilyloxy)furan and Enones

AU - Wang, Ying

AU - Du, Guang Fen

AU - Xing, Fen

AU - Huang, Kuo-Wei

AU - Dai, Bin

AU - He, Lin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Shihezi University[2012ZRKXJQ06]

PY - 2015/10/15

Y1 - 2015/10/15

N2 - N-heterocyclic carbenes have been utilised as highly efficient nucleophilic organocatalysts to mediate vinylogous Mukaiyama/Michael reactions of 2-(trimethylsilyloxy)furan with enones to afford γ-substituted butenolides in 44-99% yield with 3:1-32:1 diastereoselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - N-heterocyclic carbenes have been utilised as highly efficient nucleophilic organocatalysts to mediate vinylogous Mukaiyama/Michael reactions of 2-(trimethylsilyloxy)furan with enones to afford γ-substituted butenolides in 44-99% yield with 3:1-32:1 diastereoselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

UR - http://hdl.handle.net/10754/594176

UR - http://doi.wiley.com/10.1002/ajoc.201500348

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DO - 10.1002/ajoc.201500348

M3 - Article

SN - 2193-5807

VL - 4

SP - 1362

EP - 1365

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 12

ER -

N-Heterocyclic-Carbene-Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2-(Trimethylsilyloxy)furan and Enones

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