Issue 24, 2022

Synthesis of 2-acetal-1,3-enynes by Sonogashira reaction of bromovinyl acetals with alkynes: application to the formal synthesis of a glucagon antagonist

Abstract

The preparation of functionalized 1,3-enynes bearing an acetal moiety at the 2-position has been studied through Sonogashira reaction of bromovinyl acetals with various alkyl- and aryl-substituted terminal alkynes. The palladium-catalyzed coupling reaction tolerated a wide substrate scope and a range of 2-acetal-1,3-enynes were obtained in up to 87% yield under mild conditions that could be transposed to multi-gram scale. This protocol has been applied to the preparation of a key intermediate in the synthesis of a glucagon antagonist.

Graphical abstract: Synthesis of 2-acetal-1,3-enynes by Sonogashira reaction of bromovinyl acetals with alkynes: application to the formal synthesis of a glucagon antagonist

Supplementary files

Article information

Article type
Paper
Submitted
29 Mar 2022
Accepted
02 May 2022
First published
09 May 2022

New J. Chem., 2022,46, 11492-11501

Synthesis of 2-acetal-1,3-enynes by Sonogashira reaction of bromovinyl acetals with alkynes: application to the formal synthesis of a glucagon antagonist

L. Bacheley, Q. Llopis, A. Westermeyer, G. Guillamot, P. Phansavath and V. Ratovelomanana-Vidal, New J. Chem., 2022, 46, 11492 DOI: 10.1039/D2NJ01541B

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