Aldehyde Umpolung by N-Heterocyclic Carbenes: NMR Characterization of the Breslow Intermediate in its Keto Form, and a Spiro-Dioxolane as the Resting State of the Catalytic System

Aldehyde Umpolung by N-Heterocyclic Carbenes: NMR Characterization of the Breslow Intermediate in its Keto Form, and a Spiro-Dioxolane as the Resting State of the Catalytic System

Surprises from a classic: The Breslow intermediate of triazolylidene‐catalyzed benzoin condensations was characterized for the first time by NMR spectroscopy in its keto form (K, energetic minimum). The hitherto unknown spiro‐dioxolane S, generated from the carbene catalyst and two equivalents of al...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-09, Vol.49 (39), p.7120-7124
Hauptverfasser: Berkessel, Albrecht, Elfert, Silvia, Etzenbach-Effers, Kerstin, Teles, J. Henrique
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carbenes
NMR spectroscopy
organocatalysis
reaction mechanisms
umpolung
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container_issue 39
container_start_page 7120
container_title Angewandte Chemie (International ed.)
container_volume 49
creator Berkessel, Albrecht
Elfert, Silvia
Etzenbach-Effers, Kerstin
Teles, J. Henrique
description Surprises from a classic: The Breslow intermediate of triazolylidene‐catalyzed benzoin condensations was characterized for the first time by NMR spectroscopy in its keto form (K, energetic minimum). The hitherto unknown spiro‐dioxolane S, generated from the carbene catalyst and two equivalents of aldehyde, is the resting state of the catalytic system.
doi_str_mv 10.1002/anie.200907275
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subjects carbenes
NMR spectroscopy
organocatalysis
reaction mechanisms
umpolung
title Aldehyde Umpolung by N-Heterocyclic Carbenes: NMR Characterization of the Breslow Intermediate in its Keto Form, and a Spiro-Dioxolane as the Resting State of the Catalytic System
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