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Nitrogen inversion as a diastereomeric relay in azasugar synthesis: the first synthesis of adenophorine.

Abstract:
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.
Publication status:
Published

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Publisher copy:
10.1002/anie.200351002

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Journal:
Angewandte Chemie (International ed. in English)
Volume:
42
Issue:
32
Pages:
3788-3792
Publication date:
2003-08-05
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
URN:
uuid:def53f27-2a47-4cb8-8edc-e3193cf6d5c3
Source identifiers:
38778
Local pid:
pubs:38778

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