Alkenenitriles:: Annulations with ω-chloro Grignard reagents

被引:14
作者
Fleming, FF [1 ]
Zhang, ZY [1 ]
Wang, QZ [1 ]
Steward, OW [1 ]
机构
[1] Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA
关键词
D O I
10.1021/ol0261175
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] 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.
引用
收藏
页码:2493 / 2495
页数:3
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