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Issue 75, 2019
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The base-catalysed Tamura cycloaddition reaction: calculation, mechanism, isolation of intermediates and asymmetric catalysis

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Abstract

A combined experimental and computational investigation has revealed that the base-catalysed Tamura cycloaddition between homophthalic anhydride and activated alkenes/alkynes – a reaction previously thought of as a Diels–Alder type process – proceeds via a stepwise mechanism involving conjugate addition and ring closure; which allowed the first catalytic asymmetric α-substitution reactions to be demonstrated with up to >99% ee.

Graphical abstract: The base-catalysed Tamura cycloaddition reaction: calculation, mechanism, isolation of intermediates and asymmetric catalysis

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Supplementary files

Article information


Submitted
02 Jul 2019
Accepted
12 Aug 2019
First published
02 Sep 2019

Chem. Commun., 2019,55, 11283-11286
Article type
Communication

The base-catalysed Tamura cycloaddition reaction: calculation, mechanism, isolation of intermediates and asymmetric catalysis

B. Lockett-Walters, C. Trujillo, B. Twamley and S. Connon, Chem. Commun., 2019, 55, 11283
DOI: 10.1039/C9CC05064G

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