Issue 6, 2017

Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives

Abstract

A phosphine-mediated domino reaction between phthalimidomalonates and allenoates furnishes highly functionalized pyrroloisoindolinone derivatives in synthetically useful yields. When ethyl but-2-ynoate was reacted with phthalimidomalonates under the same conditions, pyrroloisoindolinone derivatives were also obtained in good to excellent yields. The mechanism for the transformation is a tandem γ-umpolung/Wittig/γ-umpolung process. The present domino reaction not only exploits the potential of allenoates, but also extends the existing phosphine-mediated cyclization scope.

Graphical abstract: Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
02 Mud 2016
Accepted
02 Ama 2017
First published
04 Ama 2017

Org. Chem. Front., 2017,4, 967-971

Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives

Z. Huang, Q. Chen, X. Yang, Y. Liu, L. Zhang, T. Lu and Q. Zhou, Org. Chem. Front., 2017, 4, 967 DOI: 10.1039/C6QO00775A

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