Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid Derived N??Acyliminium Ions

…, H Hiemstra, HE Schoemaker

Index: Rutjes, Floris P. J. T.; Veerman, Johan J. N.; Meester, Wim J. N.; Hiemstra, Henk; Schoemaker, Hans E. European Journal of Organic Chemistry, 1999 , # 5 p. 1127 - 1135

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Citation Number: 35

Abstract

Abstract 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 ...