Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.
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.
O'Donnell
Martin J
MJ
Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, USA. odonnell@chem.iupui.edu
Cooper
Jeremy T
JT
Mader
Mary M
MM
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
D000596:Amino Acids; D000613:Aminobutyrates; D001880:Boranes; D002930:Cinchona Alkaloids; D007532:Isoleucine; C010535:2-amino-3-phenylbutanoic acid