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ChemInform Abstract: Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid Derived N-Acyliminium Ions.

✍ Scribed by Floris P. J. T. Rutjes; Johan J. N. Veerman; Wim J. N. Meester; Henk Hiemstra; Hans E. Schoemaker

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

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 yields. The reaction mechanism of this cyclization including an aza-Cope equilibrium is discussed. Additionally, the synthesis of a novel vinylsilane-containing amino acid (IV) is presented, involving the enzymatic resolution of amino acid amide (III) as key step. -(RUTJES, FLORIS P.

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