Stereocontrolled synthesis of 3-(trans-2-aminocyclopropyl)alanine, a key component of belactosin A.
Herein we report a concise synthesis of 3-(trans-2-aminocyclopropyl)alanine, a component of belactosin A, using asymmetric alkylation of a glycine enolate in the presence of chiral phase-transfer catalysts to control the configuration at C2. Reaction of protected glycidol with triethyl phosphonoacetate (Wadsworth-Emmons cyclopropanation) is used for enantiospecific preparation of an intermediate cyclopropanecarboxylate that is converted to a cyclopropylamine via Curtius rearrangement. [reaction: see text]
Armstrong
Alan
A
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK. a.armstrong@imperial.ac.uk
Scutt
James N
JN
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000478:Alkylation; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives; D036341:Intercellular Signaling Peptides and Proteins; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; C406052:belactosin A; D000409:Alanine; D005998:Glycine