Synthesis of Azasugars through a Proline-Catalyzed Reaction

We report an efficient route to obtain azasugars from the enantiomerically pure l- and d-diethyltartrate. The key step is a proline-catalyzed aldol condensation, in which both enantiomers of proline have been used as catalyst, affording complementary anti-aldol products.

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2006-08, Vol.71 (16), p.6258-6261
Hauptverfasser:	Calderón, Félix, Doyagüez, Elisa G, Fernández-Mayoralas, Alfonso
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Aza Compounds - chemical synthesis Aza Compounds - chemistry Carbohydrates - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Hydrogen - chemistry Molecular Structure Organic chemistry Proline - chemistry Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:	We report an efficient route to obtain azasugars from the enantiomerically pure l- and d-diethyltartrate. The key step is a proline-catalyzed aldol condensation, in which both enantiomers of proline have been used as catalyst, affording complementary anti-aldol products.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo060568b