194796-77-5Relevant academic research and scientific papers
Asymmetric Synthesis of Unsaturated Pipecolic Acid Derivatives
Agami, Claude,Bihan, Dominique,Morgentin, Rémy,Puchot-Kadouri, Cathy
, p. 799 - 800 (1997)
Two enantiopure pipecolic acid derivatives having an olefinic moiety were synthesized from an intramolecular addition of allyl silanes on an iminium double bond. The iminium moiety was generated via a reaction of chiral β-amino alcohols with glyoxal.
Asymmetric syntheses of enantiopure 4-substituted pipecolic acid derivatives
Agami, Claude,Bisaro, Fabrice,Comesse, Sebastien,Guesne, Sebastien,Kadouri-Puchot, Catherine,Morgentin, Remy
, p. 2385 - 2389 (2007/10/03)
(2R,4R)-4-Methylpipecolic acid and (2S,4R)-4-hydroxypipecolic acid, two biologically active amino acids, were synthesized using the same strategy. A third amino acid, obtained in a protected form, was also obtained in the same way. The key step of these syntheses involves an intramolecular eneiminium cyclization which occurs with complete stereoselectivity. The resulting exocyclic double bond can react in a diastereoselective way to afford pure lactones, which can then be efficiently converted into the amino acids.
