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

2003; Wiley; Volume: 42; Issue: 32 Linguagem: Inglês

10.1002/anie.200351002

1521-3773

Michael A. T. Maughan, Ieuan G. Davies, Timothy D. W. Claridge, Steve Courtney, Phil Hay, Benjamin G. Davis,

Legume Nitrogen Fixing Symbiosis

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.