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: orgywjzstu.edu.cn

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

DOI: 10.1055/s-0037-1612255

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Abstract

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

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ID: J72-Y2019