HEXAFLUOROACETONE AS ACTIVATING AND PROTECTING REAGENT IN AMINO-ACID AND PEPTIDE CHEMISTRY .19. AN EFFICIENT APPROACH TO THE FAMILY OF 4-SUBSTITUTED PIPECOLIC ACIDS - SYNTHESES OF 4-OXO-HYDROXY-L-PIPECOLIC, CIS-4-HYDROXY-L-PIPECOLIC, AND TRANS-4-HYDROXY-L-PIPECOLIC ACIDS FROM L-ASPARTIC ACID

被引:41
作者
GOLUBEV, A
SEWALD, N
BURGER, K
机构
[1] UNIV LEIPZIG,INST ORGAN CHEM,D-04103 LEIPZIG,GERMANY
[2] RUSSIAN ACAD SCI,INEOS,MOSCOW 117813,RUSSIA
关键词
D O I
10.1016/0040-4039(95)00183-D
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Oxo-L-pipecolic acid, 4-hydroxy-L-pipecolic acids, L-aspartic acid, hexafluoroacetone, intramolecular Michael addition, Stille reaction.
引用
收藏
页码:2037 / 2040
页数:4
相关论文
共 22 条
[1]   ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES [J].
AGAMI, C ;
COUTY, F ;
POURSOULIS, M ;
VAISSERMANN, J .
TETRAHEDRON, 1992, 48 (03) :431-442
[2]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[3]  
BURGER K, 1990, CHEM ZTG, V114, P249
[4]  
BURGER VK, 1991, CHEM ZTG, V115, P77
[5]   4-HYDROXYPIPECOLIC ACID FRM ACACIA SPECIES, AND ITS STEREOISOMERS [J].
CLARKLEWIS, J ;
MORTIMER, PI .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JAN) :189-&
[6]   A FLUORINE-MEDIATED BORON REDUCING AGENT - SODIUM TRIS(PENTAFLUOROPHENOXY)BOROHYDRIDE - PREPARATION AND REACTION WITH SELECTED ORGANIC-COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS - FACILE DIASTEREOSELECTIVE REDUCTION OF SUBSTITUTED CYCLOHEXANONES [J].
FULLER, JC ;
KARPINSKI, ML ;
WILLIAMSON, SM ;
SINGARAM, B .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 66 (02) :123-128
[7]   A SHORT SYNTHESIS OF 4-KETOPIPECOLIC ACID HYDROCHLORIDE [J].
HARTMANN, P ;
OBRECHT, JP .
SYNTHETIC COMMUNICATIONS, 1988, 18 (06) :553-557
[8]   SYNTHESIS OF CIS-4-(PHOSPHONOOXY)-2-PIPERIDINECARBOXYLIC ACID, AN N-METHYL-D-ASPARTATE ANTAGONIST [J].
HAYS, SJ ;
MALONE, TC ;
JOHNSON, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :4084-4086
[9]   AMINO-ACIDS .12. (+/-)PIPECOLIC ACID-DERIVATIVES .2. AN EXPEDIENT SYNTHETIC ENTRY TO SUBSTITUTED PIPECOLIC ACIDS [J].
HERDEIS, C ;
ENGEL, W .
ARCHIV DER PHARMAZIE, 1992, 325 (07) :419-423
[10]  
JACKSON RFW, 1994, TETRAHEDRON LETT, V35, P4419