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.

Electrophoretic Deposition Polymerization of Diacetylenes with Tunable Structure

“…DA monomers 1 are constructed from four parts, 2(5 H )‐furanone, L ‐menthol, amino acid, and propargyl bromide, and the former three units may make 1 have multiple chiral centers (Scheme S1, Supporting Information), which can easily bring the novel chiral PDAs with tunable structure. Particularily, amino acid is a kind of important inexpensive functional synthon extensively used in many fields, this structure unit has more changeability in the group R 1 or its main chain (Scheme ). Furthermore, double hydrogen‐bonding interactions from amino acid unit can enhance the formation of stable PDA backbone, and amino acid unit as polar groups of the side chain in PDA may induce the conformation change of PDA backbone with a chromatic transition .…”

(R)-α-Aminoadipic Acid: A Versatile Precursor for the Synthesis of D-Amino Acids

“…We previously disclosed the syntheses of alcohol 4 , enamine 5 , and aldehyde 6 from ( R )- α -aminoadipic acid (Scheme 1) [10, 11]. …”

“…In the pharmaceutical semisynthesis of cephalosporin derivatives, the central intermediate 7-aminocephalosporanic acid (7-ACA) is obtained by enzymatic cleavage of the fermentation product cephalosporin C (CephC) [9]. As the enantiomerically pure ( R )- α -aminoadipic acid is available from this process on a large scale, we embarked on a project to explore the application of this chiral pool building block for the synthesis of ( R )-pipecolic acid and its derivatives [10, 11]. …”

Synthesis of Benzimidazoles from Amino Acids with Solvent-free Melting Method

“…As a kind of natural biological resource with physiological activities, inexpensive amino acids are extensively used in organic synthesis [12][13][14][15][16] . Especially, when they are applied to synthesize benzimidazoles, the products with amino group are excellent ligands in coordination chemistry and asymmetric synthesis [17][18][19][20][21] .…”