Alkenenitriles: annulations with omega-chloro Grignard reagents.
[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.
Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA. flemingf@duq.edu
Fraser F
FF
Fleming
Zhiyu
Z
Zhang
Qunzhao
Q
Wang
Omar W
OW
Steward
D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002614:Chelating Agents / Q000737:chemistry; D003500:Cyclization; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis; D008274:Magnesium / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis; D009570:Nitriles / Q000737:chemistry*
D000475:Alkenes; D002614:Chelating Agents; D006844:Hydrocarbons, Cyclic; D009281:Naphthalenes; D009570:Nitriles; C007229:decalin; D008274:Magnesium