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- Title
Single-Electron/Pericyclic Cascade for the Synthesis of Dienes.
- Authors
Campbell, Natalie E.; Sammis, Glenn M.
- 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.
- Subjects
PERICYCLIC reactions; DIOLEFINS; RING formation (Chemistry); ALDEHYDES; STEREOSELECTIVE reactions; DIAZENES
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 24, p6342
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201403234