This work was partially supported by the Toray Science Foundation, and a Grant-in-Aid for Scientific Research from MEXT. S.S. is grateful to the Japan Society for the Promotion of Science (JSPS) for a postdoctoral fellowship.
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Zuschrift
Asymmetric Diels–Alder Reactions of α,β-Unsaturated Aldehydes Catalyzed by a Diarylprolinol Silyl Ether Salt in the Presence of Water†
Article first published online: 21 JUL 2008
DOI: 10.1002/ange.200801408
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Hayashi, Y., Samanta, S., Gotoh, H. and Ishikawa, H. (2008), Asymmetric Diels–Alder Reactions of α,β-Unsaturated Aldehydes Catalyzed by a Diarylprolinol Silyl Ether Salt in the Presence of Water. Angewandte Chemie, 120: 6736–6739. doi: 10.1002/ange.200801408
- †
Publication History
- Issue published online: 8 AUG 2008
- Article first published online: 21 JUL 2008
- Manuscript Revised: 28 MAY 2008
- Manuscript Received: 24 MAR 2008
Funded by
- Toray Science Foundation
- Grant-in-Aid for Scientific Research
- Japan Society for the Promotion of Science
Keywords:
- Asymmetrische Synthesen;
- Cycloadditionen;
- Enantioselektivität;
- Organokatalyse;
- Wasserchemie
Graphical Abstract
Vornehmlich dasexo-Isomer liefert die Titelreaktion (siehe Schema; TMS=Trimethylsilyl), die ohne organisches Lösungsmittel auskommt und bei der die Produkte durch Destillation isoliert werden können. Wasser erhöht sowohl die Geschwindigkeit der Reaktion als auch ihre Enantioselektivität.