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Alkenenitriles: annulations with omega-chloro Grignard reagents
Fraser F Fleming1, Zhiyu Zhang, Qunzhao Wang
1Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA. flemingf@duq.edu
Organic Letters
|July 19, 2002
Abstract:
[reaction: see text] omega-Chloro Grignard reagents chelate with cyclic gamma-hydroxy-alpha,beta-alkenenitriles to trigger a conjugate addition-alkylation annulation. The chelation-controlled conjugate addition-alkylation is the first anionic annulation with alpha, beta-alkenenitriles, providing cis bicyclo[3.3.0]octane, hydrindane, and decalin ring systems in a single synthetic operation.