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Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid Derived N ‐Acyliminium Ions
Author(s) -
Rutjes Floris P. J. T.,
Veerman Johan J. N.,
Meester Wim J. N.,
Hiemstra Henk,
Schoemaker Hans E.
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199905)1999:5<1127::aid-ejoc1127>3.0.co;2-a
Subject(s) - chemistry , enantiopure drug , pipecolic acid , amino acid , derivatization , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry , high performance liquid chromatography , catalysis
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.