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

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

doi:10.1055/s-0035-1560833

Synthesis, Table of Contents

Synthesis 2016; 48(01): 79-84
DOI: 10.1055/s-0035-1560833

paper

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

Ying Wang

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China Email: duguangfen@shzu.edu.cn

,

Fen Xing

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China Email: duguangfen@shzu.edu.cn

,

Mei Xue

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China Email: duguangfen@shzu.edu.cn

,

Guang-Fen Du*

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China Email: duguangfen@shzu.edu.cn

^bLaboratory of Materials-Oriented Chemical Engineering of Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China

,

Xu-Hong Guo

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China Email: duguangfen@shzu.edu.cn

^bLaboratory of Materials-Oriented Chemical Engineering of Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China

,

Kuo-Wei Huang

^cDivision of Chemical and Life Sciences & Engineering, and Catalysis Center, King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia

,

Bin Dai

^aSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, 832000 Shihezi, P. R. of China Email: duguangfen@shzu.edu.cn

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Abstract

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Abstract

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.

Key words

N-heterocyclic carbene - NHC - vinylogous Mukaiyama aldol reaction - 2-(trimethysilyloxy)furan - butenolide

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References

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