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

Bruce Lockett-Walters; Cristina Trujillo; Brendan Twamley; Stephen Connon

doi:10.1039/c9cc05064g

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

Bruce Lockett-Walters, Cristina Trujillo^*, Brendan Twamley, Stephen Connon

^*Corresponding author for this work

Computational and Theoretical Chemistry

University of Dublin Trinity College

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	11283-11286
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	75
Early online date	2 Sept 2019
DOIs	https://doi.org/10.1039/c9cc05064g
Publication status	Published - 25 Sept 2019

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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.",

author = "Bruce Lockett-Walters and Cristina Trujillo and Brendan Twamley and Stephen Connon",

note = "Funding Information: This publication has emanated from research supported by the Science Foundation Ireland (SFI – 12-IA-1645). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2019.",

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AU - Trujillo, Cristina

AU - Twamley, Brendan

AU - Connon, Stephen

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Y1 - 2019/9/25

N2 - 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.

AB - 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.

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JO - Chemical Communications

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ER -

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

Abstract

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