Issue 17, 2021

The transition-metal-catalyzed stereoselective ring-expansion of vinylaziridines and vinyloxiranes

Abstract

The transition-metal-aided stereoselective construction of sp3-carbon-rich heterocyclic scaffolds using strained-ring systems has received considerable attention in recent years due to the prominent presence of these scaffolds in myriad natural products, bioactive molecules, and pharmaceutical components. In this area, the catalytic ring-enlargement of vinylaziridines and vinyloxiranes plays a predominant role when synthesizing high sp3-content biorelevant heterocyclic compounds. This article aims to portray recent advancements in the ring-expansion of vinylaziridines and vinyloxiranes for accessing densely functionalized stereoselective heterocycles that have been developed over the past five years, with an emphasis on the substrate scopes and mechanistic insights into the key methodologies, and it is arranged based on the transition metals used and the ring sizes of the heterocyclic scaffolds.

Graphical abstract: The transition-metal-catalyzed stereoselective ring-expansion of vinylaziridines and vinyloxiranes

Article information

Article type
Review Article
Submitted
09 Feb 2021
Accepted
31 Mar 2021
First published
31 Mar 2021

Org. Biomol. Chem., 2021,19, 3776-3790

The transition-metal-catalyzed stereoselective ring-expansion of vinylaziridines and vinyloxiranes

T. Sarkar, K. Talukdar, B. K. Das, T. A. Shah, B. Debnath and T. Punniyamurthy, Org. Biomol. Chem., 2021, 19, 3776 DOI: 10.1039/D1OB00259G

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