title: Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.
abstract: Optically active syn- or anti-beta-substituted-alpha-amino acid derivatives are prepared in 94 to >/=99% ee and 66-98% ds by reaction of the Schiff base acetate of glycine tert-butyl ester with chiral, nonracemic B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine (CdOH) or cinchonine (CnOH), base, and lithium chloride.
authors.affiliation: Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, USA. odonnell@chem.iupui.edu
authors.forename: Martin J
authors.initials: MJ
authors.lastname: O'Donnell
authors.forename: Jeremy T
authors.initials: JT
authors.lastname: Cooper
authors.forename: Mary M
authors.initials: MM
authors.lastname: Mader
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis*; D000613:Aminobutyrates / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D002930:Cinchona Alkaloids / Q000737:chemistry; D007532:Isoleucine / Q000031:analogs & derivatives; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000596:Amino Acids; D000613:Aminobutyrates; D001880:Boranes; D002930:Cinchona Alkaloids; D007532:Isoleucine; C010535:2-amino-3-phenylbutanoic acid