Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid DerivedN-Acyliminium Ions
1999; Wiley; Volume: 1999; Issue: 5 Linguagem: Inglês
10.1002/(sici)1099-0690(199905)1999
ISSN1434-193X
AutoresFloris P. J. T. Rutjes, Johan J. N. Veerman, Wim J. N. Meester, Henk Hiemstra, Hans E. Schoemaker,
Tópico(s)Chemical Synthesis and Analysis
ResumoThe 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.
Referência(s)