A new enantioselective synthesis of (2S)-pipecolic acid

被引:15
作者
Agami, C [1 ]
Kadouri-Puchot, C [1 ]
Kizirian, JC [1 ]
机构
[1] Univ Paris 06, CNRS, Lab Synth Asymetr Assoc, F-75005 Paris, France
关键词
D O I
10.1080/00397910008087421
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of enantiomerically pure (2S)-pipecolic acid, involving a highly diastereoselective reaction between iminium ion and vinylsilane moieties, is described.
引用
收藏
页码:2565 / 2572
页数:8
相关论文
共 18 条
[1]  
Agami C, 1997, SYNLETT, P799
[2]  
Agami C, 1998, EUR J ORG CHEM, V1998, P2461
[3]   ASYMMETRIC-SYNTHESIS .32. A NEW ACCESS TO ENANTIOMERICALLY PURE (S)-(-)-PIPECOLIC ACID AND 2-ALKYLATED OR 6-ALKYLATED DERIVATIVES [J].
BERRIEN, JF ;
ROYER, J ;
HUSSON, HP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3769-3774
[4]   (-)-Sandramycin: Total synthesis and characterization of DNA binding properties [J].
Boger, DL ;
Chen, JH ;
Saionz, KW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) :1629-1644
[5]   SUBSTITUTION OF PROLINE WITH PIPECOLIC ACID AT THE SCISSILE BOND CONVERTS A PEPTIDE SUBSTRATE OF HIV PROTEINASE INTO A SELECTIVE INHIBITOR [J].
COPELAND, TD ;
WONDRAK, EM ;
TOZSER, J ;
ROBERTS, MM ;
OROSZLAN, S .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 169 (01) :310-314
[6]   AN ACYL-IMINIUM ION CYCLIZATION ROUTE TO A NOVEL CONFORMATIONALLY RESTRICTED DIPEPTIDE MIMIC - APPLICATIONS TO ANGIOTENSIN-CONVERTING ENZYME-INHIBITION [J].
FLYNN, GA ;
GIROUX, EL ;
DAGE, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7914-7915
[7]   SYNTHESIS AND REACTIONS OF ALPHA-(TRIFLUROMETHANESULFONYLOXY)ENECARBAMATES PREPARED FROM N-ACYLLACTAMS [J].
FOTI, CJ ;
COMINS, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2656-2657
[8]   Convenient resolution of (+/-)-piperidine-2-carboxylic acid ((+/-)-pipecolic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(-)-1-[1-(dimethylamino)ethyl]naphthalene [J].
Hockless, DCR ;
Mayadunne, RC ;
Wild, SB .
TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :3031-3037
[9]   TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506 [J].
JONES, TK ;
MILLS, SG ;
REAMER, RA ;
ASKIN, D ;
DESMOND, R ;
VOLANTE, RP ;
SHINKAI, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1157-1159
[10]   SELECTIVE-INHIBITION OF THROMBIN BY (2R,4R)-4-METHYL-1-[N2-[(3-METHYL-1,2,3,4-TETRAHYDRO-8-QUINOLINYL)SULFONYL]-L-ARGINYL)]-2-PIPERIDINECARBOXYLIC ACID [J].
KIKUMOTO, R ;
TAMAO, Y ;
TEZUKA, T ;
TONOMURA, S ;
HARA, H ;
NINOMIYA, K ;
HIJIKATA, A ;
OKAMOTO, S .
BIOCHEMISTRY, 1984, 23 (01) :85-90