225656-31-5Relevant articles and documents
Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions
Rutjes, Floris P. J. T.,Veerman, Johan J. N.,Meester, Wim J. N.,Hiemstra, Henk,Schoemaker, Hans E.
, p. 1127 - 1135 (2007/10/03)
The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.