Issue 16, 2024

A domino [3 + 2] cycloaddition/deamination/imine hydrolysis reaction of cyclopropyl spirooxindoles with thiourea for access to spiro-γ-thiolactone oxindoles

Abstract

A domino [3 + 2] cycloaddition/deamination/imine hydrolysis reaction of D–A cyclopropane with inexpensive thiourea catalyzed by Lu(OTf)3 has been developed. A series of γ-thiolactone spirooxindole compounds with potential biological activity were obtained in up to 98% yields. Experiments to investigate the mechanism showed that γ-thiolactone products were from the hydrolysis of the imine intermediates. In addition, the asymmetric catalytic reaction of D–A cyclopropane and thiourea has been successfully developed to afford spiro-γ-thiolactone compounds with good enantioselectivities (up to 98% ee). The utility of this method was showcased by the facile transformation and biological activity of products.

Graphical abstract: A domino [3 + 2] cycloaddition/deamination/imine hydrolysis reaction of cyclopropyl spirooxindoles with thiourea for access to spiro-γ-thiolactone oxindoles

Supplementary files

Article information

Article type
Research Article
Submitted
12 May 2024
Accepted
14 Jun 2024
First published
15 Jun 2024

Org. Chem. Front., 2024,11, 4416-4422

A domino [3 + 2] cycloaddition/deamination/imine hydrolysis reaction of cyclopropyl spirooxindoles with thiourea for access to spiro-γ-thiolactone oxindoles

H. Wang, X. Wen, X. Xu, D. Wang and H. Guo, Org. Chem. Front., 2024, 11, 4416 DOI: 10.1039/D4QO00833B

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