Issue 3, 2022

Synthesis of functionalized 3,2′-pyrrolidinyl spirooxindoles via domino 1,6-addition/annulation reactions of para-quinone methides and 3-chlorooxindoles

Abstract

A highly efficient base-mediated diastereoselective [4 + 1] cycloaddition of ortho-tosylaminophenyl-substituted p-QMs with 3-chlorooxindoles has been developed to afford 3,2′-pyrrolidinyl spirooxindoles in high yields with high diastereoselectivity through a domino 1,6-addition/cyclization sequence. This reaction exhibits broad substrate scope and excellent functional group tolerance.

Graphical abstract: Synthesis of functionalized 3,2′-pyrrolidinyl spirooxindoles via domino 1,6-addition/annulation reactions of para-quinone methides and 3-chlorooxindoles

Supplementary files

Article information

Article type
Research Article
Submitted
25 Oct 2021
Accepted
17 Dec 2021
First published
20 Dec 2021

Org. Chem. Front., 2022,9, 615-626

Synthesis of functionalized 3,2′-pyrrolidinyl spirooxindoles via domino 1,6-addition/annulation reactions of para-quinone methides and 3-chlorooxindoles

X. Tian, Y. Zhang, W. Ren and Y. Wang, Org. Chem. Front., 2022, 9, 615 DOI: 10.1039/D1QO01605A

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