title: Radical Cyclization in Heterocycle Synthesis. 6.(1) A New Entry to Cyclic Amino Alcohols via Stannyl Radical Cyclization of Oxime Ethers Connected with Aldehydes or Ketones.
abstract: Oxime ethers connected by a tether to aldehydes or ketones efficiently cyclize via stannyl radical addition-cyclization to provide a new entry to cyclic amino alcohols. Upon treatment with tributyltin hydride in the presence of AIBN, oxime ethers connected with either an aldehyde or a ketone via a nitrogen atom smoothly underwent stannyl radical addition-cyclization to give five- to seven-membered cis- and trans-heterocyclic amino alcohols of which the trans-isomers were major products. The newly found radical cyclization provides a novel method for preparing not only bifunctionalized heterocyclic compounds but also adjacently functionalized amino alcohols carrying two quaternary carbons.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
authors.forename: Takeaki
authors.initials: T
authors.lastname: Naito
authors.forename: Kazumi
authors.initials: K
authors.lastname: Nakagawa
authors.forename: Takako
authors.initials: T
authors.lastname: Nakamura
authors.forename: Akira
authors.initials: A
authors.lastname: Kasei
authors.forename: Ichiya
authors.initials: I
authors.lastname: Ninomiya
authors.forename: Toshiko
authors.initials: T
authors.lastname: Kiguchi