Nitrogen Inversion as a Diastereomeric Relay in Azasugar Synthesis: The First Synthesis of Adenophorine

A temperature‐dependent relay of chirality is based on the inversion of the nitrogen lone pair in cyclic azasugars. Elimination from the conformation preferred at a given temperature leads to a cyclic imine, and in a subsequent nucleophilic attack the stereochemical information is relayed.

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Bibliographische Detailangaben
Veröffentlicht in:	Angewandte Chemie International Edition 2003-08, Vol.42 (32), p.3788-3792
Hauptverfasser:	Maughan, Michael A. T., Davies, Ieuan G., Claridge, Timothy D. W., Courtney, Steve, Hay, Phil, Davis, Benjamin G.
Format:	Artikel
Sprache:	eng
Schlagworte:	asymmetric synthesis Aza Compounds - chemical synthesis azasugars Campanulaceae - chemistry carbohydrates Carbohydrates - chemical synthesis Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology Glucosidases - antagonists & inhibitors glycosidase inhibitors imines Imines - chemistry Magnetic Resonance Spectroscopy Nitrogen - chemistry Plant Roots - chemistry stereodynamics Stereoisomerism
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Beschreibung
Zusammenfassung:	A temperature‐dependent relay of chirality is based on the inversion of the nitrogen lone pair in cyclic azasugars. Elimination from the conformation preferred at a given temperature leads to a cyclic imine, and in a subsequent nucleophilic attack the stereochemical information is relayed.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200351002