Org Biomol Chem. 2016 Feb 21;14(7):2228-40. doi: 10.1039/c5ob02322j. Epub 2016 Jan 20.

Copper(I) catalyzed diastereoselective multicomponent synthesis of spiroindolo-pyrrolidines/-imidazolidines/-triazolidines from diazoamides via azomethine ylides.

Organic & biomolecular chemistry

Sengodagounder Muthusamy, Singaravelan Ganesh Kumar

PMID: 26786749 DOI: 10.1039/c5ob02322j

Abstract

Investigations of regio-, chemo- and diastereoselective studies on three- as well as four-component reactions using diazooxindoles, imines, aldehydes, amines, alkenes, alkynes or diazenes in the presence of copper(I) thiophene-2-carboxylate are performed to furnish spiroindolo-pyrrolidine/-imidazolidine/-triazolidine ring systems in good yields. A mixture of products was obtained when unsymmetrical alkenes were used as dipolarophiles. This study demonstrates the successful generation of intermolecular azomethine ylides from copper(I) carbenoids and their subsequent 1,3-dipolar cycloaddition reactions with various dipolarophiles, such as olefins (C=C), imines (C=N), diazenes (N=N) in a stereoselective manner. Single-crystal X-ray analyses were performed to establish unambiguously the structure and stereochemistry of spiroheterocyclic ring systems.

Publication Types

• Journal Article
• Research Support, Non-U.S. Gov't