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.
| Main Authors: | , , , , , |
|---|---|
| Format: | Journal article |
| Sprog: | English |
| Udgivet: |
2003
|