Divergent Synthesis of 1,6-Dicarbonyls and Sulfone-Bridged 1,7-Dicarbonyls from N-(Arylsulfonyl)acrylamides and Cyclopropanols via the Control of SO2 Insertion

2025/06/12 by Fei Chen, Ling-Yi Feng, An-Qi Zhao +13
Chemistry · #Sulfur-Based Synthesis Techniques #Chemical Synthesis and Reactions #Organic and Inorganic Chemical Reactions

paper · doi:10.1021/acs.joc.5c00677

Abstract

Preparation of two or more different products with excellent chemoselectivity from the same set of readily available substrates is a fascinating and challenging synthesis strategy. Herein, we describe the divergent synthesis of 1,6-dicarbonyls and sulfone-bridged 1,7-dicarbonyls, which bear an α-all-carbon quaternary stereocenter, from N -(arylsulfonyl)acrylamides and cyclopropanols. This reaction went through a radical cascade cyclopropyl alcohol ring-opening/selective insertion or noninsertion of the SO 2 /Truce–Smiles rearrangement process. The success of late-stage functionalization of drug derivatives and gram-scale preparation demonstrates the practical application potential of this strategy in organic synthesis and drug discovery.

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