Regio- and Stereoselective Intermolecular 1,2-Difunctionalization of Terminal Alkynes: An Approach to Access ()-β-Amidovinylsulfones.

J Org Chem

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, P.O. Box 173, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.

Published: March 2024

We have developed the first I/base-catalyzed regio- and stereoselective intermolecular β-amidosulfonylation of terminal alkynes using sodium sulfinates and quinoxalinone derivatives. The present methodology is compatible with a broad spectrum of various heterocyclic amides, terminal alkynes, and sodium sulfinates. It provides rapid access to valuable ()-β-amidovinyl sulfones at mild conditions. Moreover, the synthetic application of this methodology was demonstrated by the late-stage functionalization of numerous bioactive molecules.

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http://dx.doi.org/10.1021/acs.joc.3c02155DOI Listing

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