A DFT mechanistic study of the organocatalytic asymmetric reaction of aldehydes and homophthalic anhydride

A DFT mechanistic study of the organocatalytic asymmetric reaction of aldehydes and homophthalic anhydride

The first DFT study of the cycloaddition of benzaldehyde with homophthalic anhydride under the influence of a bifunctional organocatalyst is reported. The catalyst first binds and then deprotonates the anhydride, leading to a squaramide-bound enolate, which then adds to the aldehyde with activation...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2017, Vol.53 (63), p.8874-8877
Hauptverfasser: Trujillo, Cristina, Rozas, Isabel, Botte, Astrid, Connon, Stephen J
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creator Trujillo, Cristina
Rozas, Isabel
Botte, Astrid
Connon, Stephen J
description The first DFT study of the cycloaddition of benzaldehyde with homophthalic anhydride under the influence of a bifunctional organocatalyst is reported. The catalyst first binds and then deprotonates the anhydride, leading to a squaramide-bound enolate, which then adds to the aldehyde with activation of the electrophile by the catalyst's ammonium ion.
doi_str_mv 10.1039/c7cc04596d
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title A DFT mechanistic study of the organocatalytic asymmetric reaction of aldehydes and homophthalic anhydride
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