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

Full Text: HTML

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 ...

Related Articles:

The Synthesis of 4??Hydroxypipecolic Acids by Stereoselective Cycloaddition of Configurationally Stable Nitrones

[Cordero, Franca M.; Bonollo, Simona; Machetti, Fabrizio; Brandi, Alberto European Journal of Organic Chemistry, 2006 , # 14 p. 3235 - 3241]

Synthesis of all isomers of pulcherrimine, a bitter principle in the sea urchin ovary

[Sata, Noriko U; Kuwahara, Ryuji; Murata, Yuko Tetrahedron Letters, 2002 , vol. 43, # 1 p. 115 - 118]

Novel constrained CCK-B dipeptoid antagonists derived from pipecolic acid

[Bellier, Bruno; Da Nascimento, Sophie; Meudal, Herve; Gincel, Edith; Roques, Bernard P.; Garbay, Christiane Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 11 p. 1419 - 1424]

More Articles...