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Regiospecific Inverse‐Electron‐Demand Diels–Alder Reaction of Simultaneously Electrogenerated Diene and Dienophile: An Expeditious Route to Polyfunctionalized 1,4‐Benzoxazine Derivatives
Author(s) -
Largeron Martine,
Neudorffer Anne,
Vuilhorgne Marc,
Blattes Estelle,
Fleury MauriceBernard
Publication year - 2002
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 - 10.1002/1521-3773(20020301)41:5<824::aid-anie824>3.0.co;2-z
Subject(s) - diene , diels–alder reaction , chemistry , inverse , organic chemistry , combinatorial chemistry , catalysis , mathematics , geometry , natural rubber
The regiospecific cycloaddition of an o ‐quinone imine and a highly reactive enamine, which are electrogenerated simultaneously, can be carried out at ambient temperature in the absence of catalyst. This reaction is a powerful tool for the one‐pot synthesis of new polyfunctionalized 1,4‐benzoxazine derivatives (see scheme).