Issue 17, 2024

Diastereoselective synthesis of functionalized spiroindolines via intramolecular ipso-iodocyclization/nucleophile addition cascade reactions of indole-tethered ynones

Abstract

Herein, we describe a highly diastereoselective approach for synthesizing polyfunctionalized spiroindolines from indolyl-ynones involving an ipso-iodocyclization/nucleophile addition cascade. The developed strategy allows the formation of a spirocyclic core and the installation of two functional groups in a single operation. Also this strategy is accompanied by the generation of two C–C and one C–I bonds and two contiguous stereocenters.

Graphical abstract: Diastereoselective synthesis of functionalized spiroindolines via intramolecular ipso-iodocyclization/nucleophile addition cascade reactions of indole-tethered ynones

Supplementary files

Article information

Article type
Paper
Submitted
21 Jan 2024
Accepted
03 Apr 2024
First published
04 Apr 2024

Org. Biomol. Chem., 2024,22, 3415-3419

Diastereoselective synthesis of functionalized spiroindolines via intramolecular ipso-iodocyclization/nucleophile addition cascade reactions of indole-tethered ynones

D. Bag and S. D. Sawant, Org. Biomol. Chem., 2024, 22, 3415 DOI: 10.1039/D4OB00112E

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