Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, grant R01-GM57034), the German Academic Exchange Service (postdoctoral fellowship for M.D.), Merck Research Laboratories, and Novartis.
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Communication
Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α-Hydroxycarboxylic Acid Derivatives†
Article first published online: 18 FEB 2009
DOI: 10.1002/anie.200805805
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Dochnahl, M. and Fu, G. (2009), Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α-Hydroxycarboxylic Acid Derivatives. Angewandte Chemie International Edition, 48: 2391–2393. doi: 10.1002/anie.200805805
- †
Publication History
- Issue published online: 10 MAR 2009
- Article first published online: 18 FEB 2009
- Manuscript Received: 28 NOV 2008
Funded by
- National Institutes of Health. Grant Number: R01-GM57034
- German Academic Exchange Service
- Merck Research Laboratories
- Novartis
Keywords:
- asymmetric catalysis;
- carboxylic acids;
- cycloaddition;
- heterocycles;
- ketenes
Graphical Abstract
The appropriate choice of chiral catalyst and starting materials leads to the synthesis of 1,2-oxazetidin-3-ones by cycloadditions of ketenes with nitroso compounds with very good regioselectivity and enantioselectivity. In addition to serving as potentially bioactive target molecules, the products can be transformed into other important classes of compounds, such as α-hydroxycarboxylic acid derivatives.
Abstract
The appropriate choice of chiral catalyst and starting materials leads to the synthesis of 1,2-oxazetidin-3-ones by cycloadditions of ketenes with nitroso compounds with very good regioselectivity and enantioselectivity. In addition to serving as potentially bioactive target molecules, the products can be transformed into other important classes of compounds, such as α-hydroxycarboxylic acid derivatives.