Single-electron/pericyclic cascade for the synthesis of dienes
Natalie E Campbell1, Glenn M Sammis
1University of British Columbia, Department of Chemistry, 2036 Main Mall, Vancouver V6T 1Z1 (Canada).
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.
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