title: 6-Alkynyl- and 6-aryl-substituted (R)-pipecolic acid derivatives.
abstract: (R)-α-Aminoadipic acid is a readily available enantiomerically pure starting material for the synthesis of (R)-pipecolic acid and its derivatives. Sonogashira or Suzuki cross-coupling reactions of an N-formyl pipecolate-derived vinyl bromide furnish 6-alkynyl or aryl derivatives. Reduction with sodium cyanoborohydride and subsequent N-deformylation provide 6-alkynyl substituted (R)-pipecolic acid derivatives, valuable building blocks for amino acid and peptide chemistry.
authors.affiliation: Department of Chemistry, Bielefeld University, P.O. Box 100131, 33501 Bielefeld, Germany.
authors.forename: Amina
authors.initials: A
authors.lastname: Sadiq
authors.forename: Norbert
authors.initials: N
authors.lastname: Sewald
mesh_terms: D015074:2-Aminoadipic Acid / Q000138:chemical synthesis* / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003432:Cross-Linking Reagents; D010455:Peptides; D010875:Pipecolic Acids; D015074:2-Aminoadipic Acid