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ChemInform Abstract: Preparation of Enantiopure 4-Oxygenated Pipecolic Acid Derivatives.

✍ Scribed by Y. BOUSQUET; P. C. ANDERSON; T. BOGRI; J.-S. DUCEPPE; L. GRENIER; I. GUSE


Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
29
Category
Article
ISSN
0931-7597

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Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid Derived N-Acyliminium Ions. -N-Acyliminium ion cyclization of various non-natural olefinic amino acids (VII), (X), (XV), and (XX) in the presence of nucleophiles affords enantiopure functionalized pipecolic acids in moderate yie

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The synthesis of two enantiopure pipecolic acid esters (VI) and (XIII) is reported. Key steps are the intramolecular addition of allyl silane on an iminium double bond, generated via reaction of chiral Ξ²-amino alcohols (I) and (VII), with glyoxal (II).