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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

Berkessel, Albrecht ; Elfert, Silvia ; Etzenbach-Effers, Kerstin ; Teles, J. Henrique

Angewandte Chemie (International ed.), 2010-09, Vol.49 (39), p.7120-7124 [Periódico revisado por pares]

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Título:
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
Autor: Berkessel, Albrecht ; Elfert, Silvia ; Etzenbach-Effers, Kerstin ; Teles, J. Henrique
Assuntos: carbenes ; NMR spectroscopy ; organocatalysis ; reaction mechanisms ; umpolung
É parte de: Angewandte Chemie (International ed.), 2010-09, Vol.49 (39), p.7120-7124
Notas: http://dx.doi.org/10.1002/anie.200907275
BASF SE
istex:3C59620C4FFB5D876D77EC31D995A517A9007A2A
ark:/67375/WNG-CB187JTX-N
ArticleID:ANIE200907275
Support by BASF SE and by the Fonds der Chemischen Industrie is gratefully acknowledged. The authors thank D. Müller for providing 13C-labeled triazolylidene.
13
C‐labeled triazolylidene.
Support by BASF SE and by the Fonds der Chemischen Industrie is gratefully acknowledged. The authors thank D. Müller for providing
ObjectType-Article-1
SourceType-Scholarly Journals-1
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Descrição: 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.
Editor: Weinheim: Wiley-VCH Verlag
Idioma: Inglês

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