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Single‐Electron/Pericyclic Cascade for the Synthesis of Dienes
Author(s) -
Campbell Natalie E.,
Sammis Glenn M.
Publication year - 2014
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.201403234
Subject(s) - pericyclic reaction , cascade , aldehyde , chemistry , radical cyclization , cascade reaction , condensation , electron delocalization , combinatorial chemistry , photochemistry , organic chemistry , computational chemistry , molecule , physics , catalysis , chromatography , thermodynamics
The highly efficient and diastereoselective synthesis of E dienes has been accomplished through radical cyclization of bromoallyl hydrazones. This methodology has been further extended to generate these products through a one‐pot condensation/radical cyclization/cycloreversion cascade from simple aldehyde starting materials in high yields (>75 %) and high diastereoselectivities (>95:5). Mechanistic investigations suggest that the cascade reaction proceeds through a cyclic diazene intermediate prior to the cycloreversion.
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