Highly Diastereoselective Synthesis and Application of Functionalized 2,3-Dihydrofuran Derivatives from Enynones and Bis(diazo) Compounds.

J Org Chem

Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University, Changsha 410081, China.

Published: January 2024

A highly efficient Ag(I)-catalyzed cascade Michael addition/cyclization of enynones with 1,3-(bis)diazo compounds has been established, providing functionalized 2,3-dihydrofuran derivatives containing a diazo group and an acetylenic bond with excellent diastereoselectivity. Transformation of the diazo group and hydration of the carbon-carbon triple bond have been performed successfully in different reaction systems.

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Source
http://dx.doi.org/10.1021/acs.joc.3c01527DOI Listing

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