Issue 18, 2023

Palladium-catalyzed [4 + 3]-annulations of oxotryptamines with allyl dicarbonates: an approach toward spiro[azepane-4,3′-oxindoles]

Abstract

A novel palladium-catalyzed [4 + 3]-annulation of oxotryptamines with allyl dicarbonates has been developed. The reaction furnishes various spiro[azepane-4,3′-oxindoles] in moderate to excellent yields (30%–96%) with a Z/E ratio up to >20 : 1 through a tandem allylic substitution strategy. This protocol enables the synthesis of a wide range of seven-membered spirocyclic oxindoles with high Z-selectivity. In addition, the gram-scale reaction and further derivatizations were also investigated, demonstrating the synthetic utility of this approach.

Graphical abstract: Palladium-catalyzed [4 + 3]-annulations of oxotryptamines with allyl dicarbonates: an approach toward spiro[azepane-4,3′-oxindoles]

Supplementary files

Article information

Article type
Research Article
Submitted
14 Jun 2023
Accepted
20 Jul 2023
First published
07 Aug 2023

Org. Chem. Front., 2023,10, 4593-4597

Palladium-catalyzed [4 + 3]-annulations of oxotryptamines with allyl dicarbonates: an approach toward spiro[azepane-4,3′-oxindoles]

J. Xiao, R. Meng, X. Shi, X. Luo, H. Zhang, W. Wang, P. Xia, C. Lin and W. Su, Org. Chem. Front., 2023, 10, 4593 DOI: 10.1039/D3QO00892D

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