title: Synthesis of methyl N-Boc-(2S,4R)-4-methylpipecolate.
abstract: An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO(4)/NaIO(4) followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.
authors.affiliation: Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors.forename: Kuo-Yuan
authors.initials: KY
authors.lastname: Hung
authors.forename: Paul W R
authors.initials: PW
authors.lastname: Harris
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000478:Alkylation; D003500:Cyclization; D006865:Hydrogenation; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C556255:(2S,4R)-4-methylpipecolic acid; D010875:Pipecolic Acids; C031345:pipecolic acid