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Issue 31, 2017
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Domino carbometalation/coupling reactions of N-arylpropiolamides: a novel and promising synthetic strategy toward stereocontrolled preparation of highly substituted 3-methyleneindolinones

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Abstract

3-Methyleneindolinone derivatives are important structural motifs found in many compounds of natural occurrence and pharmacological significance. However, despite their wide importance, mild and highly efficient stereoselective synthesis of (E)- and (Z)-3-methyleneindolinones still remains to be a difficult problem. Therefore, the development of new synthetic methods for their stereocontrolled preparation is of prime importance in organic synthesis. In this mini review, we highlight the advances in stereoselective synthesis of mono- and disubstituted-3-methyleneindolinones through metal-catalyzed intramolecular cyclization of N-arylpropiolamides from 1988 to 2017.

Graphical abstract: Domino carbometalation/coupling reactions of N-arylpropiolamides: a novel and promising synthetic strategy toward stereocontrolled preparation of highly substituted 3-methyleneindolinones

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Article information


Submitted
02 Feb 2017
Accepted
08 Mar 2017
First published
29 Mar 2017

This article is Open Access

RSC Adv., 2017,7, 19061-19072
Article type
Review Article

Domino carbometalation/coupling reactions of N-arylpropiolamides: a novel and promising synthetic strategy toward stereocontrolled preparation of highly substituted 3-methyleneindolinones

E. Vessally, R. Hosseinzadeh-Khanmiri, E. Ghorbani-Kalhor, M. Es'haghi and A. Bekhradnia, RSC Adv., 2017, 7, 19061
DOI: 10.1039/C7RA01371J

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