DABCO-Catalyzed [3+2] Cycloaddition of Isatin-Derived Nitrones and Electron-Deficient Dienes via a 1,6-Addition Reaction

Abstract

Regio-, chemo-, and diastereoselective [3+2] dipolar cycloadditions of isatin-derived nitrone ylides with penta-2,4-dienenitriles have been developed. The reaction proceeds through the organic base DABCO catalyzed 1,6-addition to linear penta-2,4-dienenitriles, followed by the intramolecular cyclization. This procedure is capable of tolerating a relatively wide range of nitrone ylides under mild conditions, facilitating the preparation of various 1′-hydroxyspiro[indoline-3,2′-pyrrolidine] derivatives.

Key words

[3+2] cycloaddition - 1,6-addition - regioselectivity - nitrone ylide - spirooxindole - diastereoselectivity

Publication History

Received: 27 April 2022

Accepted after revision: 27 May 2022

Accepted Manuscript online:
27 May 2022

Article published online:
05 July 2022

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