Direct aldol reaction of pyruvic derivatives : catalytic attempt to synthesize ulosonic acids

Bibliographic description

punktacja MEiN [2012 A]: 30

title:	Direct aldol reaction of pyruvic derivatives : catalytic attempt to synthesize ulosonic acids
author:	El-Sepelgy Osama , Schwarzer Darius, Oskwarek Piotr, Młynarski Jacek
journal title:	European Journal of Organic Chemistry
volume:	2012
issue:	14
date of publication :	2012
pages:	2724-2727
ISSN:	1434-193X
eISSN:	1099-0690
DOI:	10.1002/ejoc.201200325
language:	English
journal language:	English
abstract in English:	The catalytic asymmetric aldol reaction of pyruvic aldehyde dimethyl acetal and 2-acetylthiazole with sugar aldehydes is demonstrated to be the key step in the synthesis of 3-deoxy- 2-ulosonic acids. Efficient and stereoselective pyruvate aldol reactions are catalyzed by metal-based chiral Trost and Shibasaki catalysts. The presented synthetic methodology mimics aldolase-catalyzed reactions by direct activation of C 3 pyruvate equivalents with the use of metal-based chiral cata- lysts en route to the synthesis of 2-keto-3-deoxy- D -glucosonic acid and 3-deoxy- D -manno-2-octulosonic acid derivatives.
keywords in English:	aldol reactions, asymmetric catalysis, enzymes, carbohydrates
affiliation:	Wydział Chemii : Zakład Chemii Organicznej
type:	journal article
subtype:	academic paper

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