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Direct Synthesis of β,γ-Unsaturated α-Keto Esters from Aldehydes and Pyruvates

John Kamanda Mansaray, Jiarui Sun, Shisheng Huang, Weijun Yao*

*Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China, Email:

J. K. Mansaray, J. Sun, S. Huang, W. Yao, Synlett, 2019, 30, 809-812.

DOI: 10.1055/s-0037-1612255

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A synthesis of β,γ-unsaturated α-keto esters directly from aldehydes and pyruvates is promoted by BF3•Et2O in the presence of Ac2O or by Ti(OEt)4 under mild conditions. Various aldehydes afford the desired products in good yield. Moreover, aliphatic aldehydes and Isatin were also employed to give the γ-alkyl β,γ-unsaturated α-keto esters in moderate yield with use of the Ti(OEt)4 system.

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Key Words

unsaturated α-keto esters, step economy, pyruvates, aldehydes, aldol condensation

ID: J72-Y2019