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Nitrogen Inversion as a Diastereomeric Relay in Azasugar Synthesis: The First Synthesis of Adenophorine
Author(s) -
Maughan Michael A. T.,
Davies Ieuan G.,
Claridge Timothy D. W.,
Courtney Steve,
Hay Phil,
Davis Benjamin G.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351002
Subject(s) - diastereomer , lone pair , nitrogen inversion , relay , imine , inversion (geology) , nucleophile , chirality (physics) , nitrogen , stereochemistry , chemistry , physics , organic chemistry , catalysis , symmetry breaking , molecule , paleontology , biology , chiral symmetry breaking , quantum mechanics , power (physics) , structural basin , nambu–jona lasinio model
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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