Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

Disclosed herein is an efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with alpha-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance. (c) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

Automated summary

An efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with alpha-carbonyl sulfoxonium ylides is disclosed, providing a practical access to a diverse range of multi-functionalized oxazoline derivatives with diastereoselectivity. The synthetic utility of tetra-substituted oxazolines is further demonstrated by useful manipulations into valuable building blocks of pharmaceutical relevance.