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Issue 30, 2015
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Base catalysed domino and self-domino Michael–Aldol reactions: one-pot synthesis of dispirocyclopentaneoxindoles containing multiple chiral stereocenters

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Abstract

A one-pot method for the construction of three classes of densely functionalized dispirocyclopentaneoxindoles containing multiple chiral stereocenters is developed. Base promoted self-domino and domino reactions with and without the participation of solvent, alcohol, is accomplished. Piperidine catalyzed self-domino reaction involves the participation of the nucleophilic solvent, alcohol, resulting in complex dispiro compounds containing four and five diastereoisomeric centers. Triethylamine promotes the self-domino reaction between two molecules of 3-phenacylideneoxindoles with added nucleophiles, and not with the solvent nucleophile. Diisopropylethylamine facilitates the domino reaction between 3-phenacylidineoxindole and phenacylacenaphthylenone allowing the construction of novel dispirocyclopentaneoxindoles with high yields and diastereoselectivity. A plausible mechanism is tentatively proposed to account for the diastereoselectivity of the domino Michael–Aldol reaction.

Graphical abstract: Base catalysed domino and self-domino Michael–Aldol reactions: one-pot synthesis of dispirocyclopentaneoxindoles containing multiple chiral stereocenters

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Article information


Submitted
07 Jan 2015
Accepted
19 Feb 2015
First published
19 Feb 2015

RSC Adv., 2015,5, 23291-23302
Article type
Paper
Author version available

Base catalysed domino and self-domino Michael–Aldol reactions: one-pot synthesis of dispirocyclopentaneoxindoles containing multiple chiral stereocenters

K. Suman and S. Thennarasu, RSC Adv., 2015, 5, 23291
DOI: 10.1039/C5RA00283D

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