Convenient preparations of racemic and enantiopure methyl 6-oxopipecolate

被引:38
作者
Davies, CE [1 ]
Heightman, TD [1 ]
Hermitage, SA [1 ]
Moloney, MG [1 ]
机构
[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
关键词
D O I
10.1080/00397919608086742
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Short, convenient syntheses of racemic and enantiopure methyl 6-oxopipecolate are described, starting from either pipecolic acid or (S)-lysine respectively. The sequence for the latter compound relies upon improved methodology for the oxidation of C-6 of lysine.
引用
收藏
页码:687 / 696
页数:10
相关论文
共 40 条
[1]   NEUROMEDIATOR ANALOGS - SYNTHESIS OF CIS (2R,3S) AND TRANS (2S,3S)-2,3-PIPERIDINE DICARBOXYLIC-ACIDS FROM (2S)-2-PHENYLGLYCINOL [J].
AGAMI, C ;
KADOURIPUCHOT, C ;
LEGUEN, V ;
VAISSERMANN, J .
TETRAHEDRON LETTERS, 1995, 36 (10) :1657-1660
[2]   STEREOCONTROLLED SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-ALLITOL (1-DEOXY-ALLONOJIRIMYCIN) FROM SERINE [J].
ALTENBACH, HJ ;
HIMMELDIRK, K .
TETRAHEDRON-ASYMMETRY, 1995, 6 (05) :1077-1080
[3]  
AMOROSO R, 1993, GAZZ CHIM ITAL, V123, P75
[4]   CHEMICALS FROM THE GLANDS OF ANTS [J].
ATTYGALLE, AB ;
MORGAN, ED .
CHEMICAL SOCIETY REVIEWS, 1984, 13 (03) :245-278
[5]   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
[6]   SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES, OXANES, AND THIANES [J].
BALIAH, V ;
JEYARAMAN, R ;
CHANDRASEKARAN, L .
CHEMICAL REVIEWS, 1983, 83 (04) :379-423
[7]   SYNTHESIS OF NOVEL ALPHA-AMINO-ACIDS AND DERIVATIVES USING RADICAL CHEMISTRY - SYNTHESIS OF L-ALPHA-AMINO-ADIPIC AND D-ALPHA-AMINO-ADIPIC ACIDS, L-ALPHA-AMINOPIMELIC ACID AND APPROPRIATE UNSATURATED DERIVATIVES [J].
BARTON, DHR ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
TETRAHEDRON, 1987, 43 (19) :4297-4308
[8]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM BOC DERIVATIVES OF CYCLIC AMINES [J].
BEAK, P ;
LEE, WK .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1109-1117
[9]   CHIROSPECIFIC SYNTHESIS OF (1S,3R)-1-AMINO-3-(HYDROXYMETHYL)CYCLOPENTANE, PRECURSOR FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS - DIECKMANN CYCLIZATION WITH AN ALPHA-AMINO-ACID [J].
BERGMEIER, SC ;
COBAS, AA ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2369-2376
[10]   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