N-Heterocyclic Carbene-Catalyzed Vinylogous Mukaiyama Aldol Reaction of α-Keto Esters and α-Trifluoromethyl Ketones

Guang-Fen Du; Ying Wang; Fen Xing; Mei Xue; Xu-Hong Guo; Kuo-Wei Huang; Bin Dai

doi:10.1055/s-0035-1560833

N-Heterocyclic Carbene-Catalyzed Vinylogous Mukaiyama Aldol Reaction of α-Keto Esters and α-Trifluoromethyl Ketones

Guang-Fen Du, Ying Wang, Fen Xing, Mei Xue, Xu-Hong Guo, Kuo-Wei Huang, Bin Dai

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

9 Scopus citations

Abstract

© Georg Thieme Verlag Stuttgart · New York · Synthesis 2016. N-Heterocyclic carbene (NHC)-catalyzed vinylogous Mukaiyama aldol reaction of ketones was developed. Under the catalysis of 5 mol% NHC, α-keto esters and α-trifluoromethyl ketones reacted with 2-(trimethysilyloxy)furan efficiently to produce γ-substituted butenolides containing adjacent quaternary and tertiary carbon centers in high yields with good diastereoselectivities.

Original language	English (US)
Pages (from-to)	79-84
Number of pages	6
Journal	Synthesis
Volume	48
Issue number	01
DOIs	https://doi.org/10.1055/s-0035-1560833
State	Published - Nov 4 2015

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was supported by the National Natural Science Foundation of China (Nos. 21262027, 21428302) and Shihezi University (No. 2012ZRKXJQ06). We thank Dr. L. He of Shihezi University for helpful discussions.

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10.1055/s-0035-1560833

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title = "N-Heterocyclic Carbene-Catalyzed Vinylogous Mukaiyama Aldol Reaction of α-Keto Esters and α-Trifluoromethyl Ketones",

abstract = "{\textcopyright} Georg Thieme Verlag Stuttgart · New York · Synthesis 2016. N-Heterocyclic carbene (NHC)-catalyzed vinylogous Mukaiyama aldol reaction of ketones was developed. Under the catalysis of 5 mol% NHC, α-keto esters and α-trifluoromethyl ketones reacted with 2-(trimethysilyloxy)furan efficiently to produce γ-substituted butenolides containing adjacent quaternary and tertiary carbon centers in high yields with good diastereoselectivities.",

author = "Guang-Fen Du and Ying Wang and Fen Xing and Mei Xue and Xu-Hong Guo and Kuo-Wei Huang and Bin Dai",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the National Natural Science Foundation of China (Nos. 21262027, 21428302) and Shihezi University (No. 2012ZRKXJQ06). We thank Dr. L. He of Shihezi University for helpful discussions.",

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doi = "10.1055/s-0035-1560833",

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T1 - N-Heterocyclic Carbene-Catalyzed Vinylogous Mukaiyama Aldol Reaction of α-Keto Esters and α-Trifluoromethyl Ketones

AU - Du, Guang-Fen

AU - Wang, Ying

AU - Xing, Fen

AU - Xue, Mei

AU - Guo, Xu-Hong

AU - Huang, Kuo-Wei

AU - Dai, Bin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the National Natural Science Foundation of China (Nos. 21262027, 21428302) and Shihezi University (No. 2012ZRKXJQ06). We thank Dr. L. He of Shihezi University for helpful discussions.

PY - 2015/11/4

Y1 - 2015/11/4

N2 - © Georg Thieme Verlag Stuttgart · New York · Synthesis 2016. N-Heterocyclic carbene (NHC)-catalyzed vinylogous Mukaiyama aldol reaction of ketones was developed. Under the catalysis of 5 mol% NHC, α-keto esters and α-trifluoromethyl ketones reacted with 2-(trimethysilyloxy)furan efficiently to produce γ-substituted butenolides containing adjacent quaternary and tertiary carbon centers in high yields with good diastereoselectivities.

AB - © Georg Thieme Verlag Stuttgart · New York · Synthesis 2016. N-Heterocyclic carbene (NHC)-catalyzed vinylogous Mukaiyama aldol reaction of ketones was developed. Under the catalysis of 5 mol% NHC, α-keto esters and α-trifluoromethyl ketones reacted with 2-(trimethysilyloxy)furan efficiently to produce γ-substituted butenolides containing adjacent quaternary and tertiary carbon centers in high yields with good diastereoselectivities.

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N-Heterocyclic Carbene-Catalyzed Vinylogous Mukaiyama Aldol Reaction of α-Keto Esters and α-Trifluoromethyl Ketones

Abstract

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