Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 46, Pages 16642-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja907054y
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Funding
- Deutsche Forschungsgemeinschaft (Priority Program Organocatalysis)
- Bayer-Schering Pharma AG
- Bayer Services GmbH
- BASF AG
- Sasol GmbH
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A histidine-catalyzed asymmetric direct cross-aldol reaction of enolizable aldehydes is described. In contrast to proline, histidine is able to clearly differentiate the reactivity of various aldehydes. In addition, this approach provides access to syn-configured B-hydroxyaldehydes. Thus, by application of this new methodology, defined-configuration quaternary stereocenters can be constructed with ease. The utility of this method is demonstrated in several total syntheses of branched-chain carbohydrates.
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