Formation of functionalized carbocycles via base-promoted ring opening/Brook rearrangement/allylic alkylation of gamma-silyl-beta,gamma-epoxybutanenitrile followed by nitrile anion cyclization with bis-electrophiles.
Reaction of gamma-silyl-beta,gamma-epoxybutanenitrile with a base generates an alpha-nitrile carbanion derivative of 4-siloxybut-3-enenitrile, which undergoes reaction with bis-electrophiles such as 1,omega-dihaloalkanes, omega-bromo-alpha,beta-unsaturated esters, and bisenoates to provide highly functionalized carbocycles.
Matsumoto
Tatsuya
T
Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, Minami-Ku, Hiroshima 734-8551, Japan.
Masu
Hyuma
H
Yamaguchi
Kentaro
K
Takeda
Kei
K