title: Radical addition to oxime ethers for asymmetric synthesis of beta-amino acid derivatives.
abstract: The diastereoselective alkyl radical addition to chiral oxime ethers was studied with a view to preparing enantiomerically pure alpha,beta-dialkyl-beta-amino acid derivatives. The phase transfer-catalyzed alkylation of Oppolzer's camphorsultam derivative of oxime ether proceeded smoothly to give the alkylated N-(beta-oximino)acyl derivatives. In the presence of BF3.OEt2, radical addition to the oxime ethers proceeded using triethylborane as the radical initiator to give alpha,beta-dialkyl-beta-amino acid derivatives with excellent diastereoselectivity.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
authors.forename: Hideto
authors.initials: H
authors.lastname: Miyabe
authors.forename: Kayoko
authors.initials: K
authors.lastname: Fujii
authors.forename: Takeaki
authors.initials: T
authors.lastname: Naito
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004987:Ethers; D005609:Free Radicals; D010091:Oximes