title: Tandem carbon-carbon bond-forming radical addition-cyclization reaction of oxime ether and hydrazone.
abstract: The novel tandem radical addition-cyclization of oxime ethers and hydrazones intramolecularly connected with the alpha,beta-unsaturated carbonyl group is described. The radical reaction of oxime ethers 1, 2, and 4 connected with acryloyl and methacryloyl moieties proceeded smoothly to give the heterocycles via a tandem C-C bond-forming process. The tandem reaction of hydrazone 5 took place in the presence of Zn(OTf)(2) as a Lewis acid to give the trans-cyclic product 17 without the formation of the cis-isomer. The diastereoselective radical addition-cyclization reaction of chiral oxime ether 19 was also studied. The tandem reaction of 19 proceeded smoothly even in aqueous media, providing the novel method for asymmetric synthesis of gamma-butyrolactones and beta-amino acid derivatives.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
authors.forename: Hideto
authors.initials: H
authors.lastname: Miyabe
authors.forename: Masafumi
authors.initials: M
authors.lastname: Ueda
authors.forename: Kayoko
authors.initials: K
authors.lastname: Fujii
authors.forename: Azusa
authors.initials: A
authors.lastname: Nishimura
authors.forename: Takeaki
authors.initials: T
authors.lastname: Naito