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Issue 41, 2019
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4-Hydroxymethyl-substituted oxazolidinone synthesis by tetraarylphosphonium salt-catalyzed reactions of glycidols with isocyanates

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Abstract

Preparation of 4-hydroxymethyl-substituted oxazolidinones including optically active ones, in which tetraarylphosphonium salts catalyze the reaction of glycidol with isocyanates effectively, is described. The neutral catalysis facilitates glycidol addition to isocyanates followed by intramolecular cyclization. Mechanistic studies suggest that hydrogen-bonding interactions with the catalyst play an important role in the reaction progress.

Graphical abstract: 4-Hydroxymethyl-substituted oxazolidinone synthesis by tetraarylphosphonium salt-catalyzed reactions of glycidols with isocyanates

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Submitted
12 Mar 2019
Accepted
17 Apr 2019
First published
17 Apr 2019

Chem. Commun., 2019,55, 5761-5764
Article type
Communication

4-Hydroxymethyl-substituted oxazolidinone synthesis by tetraarylphosphonium salt-catalyzed reactions of glycidols with isocyanates

Y. Toda, S. Tanaka, S. Gomyou, A. Kikuchi and H. Suga, Chem. Commun., 2019, 55, 5761
DOI: 10.1039/C9CC01983A

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