Asymmetric syntheses of pipecolic acid and derivatives

被引:71
作者
Couty, F [1 ]
机构
[1] Univ Paris 06, Lab Synthese Asymetr, F-75005 Paris, France
关键词
amino acids; pipecolic acid; pipecolic acid derivatives; asymmetric synthesis; hemisyntheses; chiral auxiliaries;
D O I
10.1007/BF01388174
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Results in the field of asymmetric synthesis of pipecolic acid derivatives are reviewed. Three sections describe the asymmetric syntheses of the title compounds (i) from the chiral pool (alpha-amino acids or carbohydrates) (ii) using a chiral auxiliary either derived from terpenes, alpha-amino acids, tartaric acid, an amine or beta-amino alcohols (iii) by means of asymmetric catalysis.
引用
收藏
页码:297 / 320
页数:24
相关论文
共 69 条
[1]  
Agami C, 1997, SYNLETT, P799
[2]   Cyclization of a chiral oxazolidine as a key-step for the synthesis of functionalized piperidines [J].
Agami, C ;
Couty, F ;
Mathieu, H .
TETRAHEDRON LETTERS, 1996, 37 (23) :4001-4002
[3]   Enantioselective synthesis of conformationally restricted analogs of NMDA: cis- and trans-piperidine-2,3-dicarboxylic acids and methylated derivatives [J].
Agami, C ;
Hamon, L ;
KadouriPuchot, C ;
LeGuen, V .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5736-5742
[4]  
AGAMI C, 1990, SYNLETT, P731
[5]   ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA CATIONIC AZA-COPE REARRANGEMENTS [J].
AGAMI, C ;
COUTY, F ;
LIN, J ;
MIKAELOFF, A ;
POURSOULIS, M .
TETRAHEDRON, 1993, 49 (33) :7239-7250
[6]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-INDOLIZIDINES 209B AND 209D VIA A HIGHLY EFFICIENT AZA-[2,3]-WITTIG REARRANGEMENT OF VINYLAZIRIDINES [J].
AHMAN, J ;
SOMFAI, P .
TETRAHEDRON, 1995, 51 (35) :9747-9756
[7]  
AKETA K, 1976, CHEM PHARM BULL, V24, P621
[8]  
ANDREWS MD, 1995, J CHEM SOC P1, P227
[9]   CHIRAL SYNTHESIS OF 5-HYDROXY-(L)-PIPECOLIC ACIDS FROM (L)-GLUTAMIC ACID [J].
BAILEY, PD ;
BRYANS, JS .
TETRAHEDRON LETTERS, 1988, 29 (18) :2231-2234
[10]   ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION [J].
BAILEY, PD ;
BROWN, GR ;
KORBER, F ;
REED, A ;
WILSON, RD .
TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1263-1282