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Facile Synthesis of Azetidine Nitrones and Diastereoselective Conversion into Densely Substituted Azetidines
Author(s) -
Reidl Tyler W.,
Son Jongwoo,
Wink Donald J.,
Anderson Laura L.
Publication year - 2017
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.201705681
Subject(s) - azetidine , cycloaddition , nucleophile , reactivity (psychology) , chemistry , nucleophilic addition , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
An electrocyclization route to azetidine nitrones from N‐alkenylnitrones was discovered that provides facile access to these unsaturated strained heterocycles. Reactivity studies showed that these compounds undergo a variety of reduction, cycloaddition, and nucleophilic addition reactions to form highly substituted azetidines with excellent diastereoselectivity. Taken together, these transformations provide a fundamentally different approach to azetidine synthesis than traditional cyclization by nucleophilic displacement and provide novel access to a variety of underexplored strained heterocyclic compounds.