Tandem base-promoted ring opening/brook rearrangement/allylic alkylation of O-silyl cyanohydrins of beta-silyl-alpha,beta-epoxyaldehydes.
[reaction: see text]. Metalated O-silyl cyanohydrins of beta-silyl-alpha,beta-epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving a base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting allylic anion.
Takeda
Kei
K
Institute of Pharmaceutical Sciences, Faculty of Medicine, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8551, Japan. takedak@hiroshima-u.ac.jp
Kawanishi
Eiji
E
Sasaki
Michiko
M
Takahashi
Yuji
Y
Yamaguchi
Kentaro
K