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Single-Electron/Pericyclic Cascade for the Synthesis of Dienes

TitleSingle-Electron/Pericyclic Cascade for the Synthesis of Dienes
Publication TypeJournal Article
Year of Publication2014
AuthorsCampbell, NE, Sammis, GM
JournalANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume53
Pagination6228-6231
Date PublishedJUN
ISSN1433-7851
Abstract

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.

DOI10.1002/anie.201403234