How to build optically active α-amino acids

被引:53
作者
Calmes, M
Daunis, J
机构
[1] Univ Montpellier 1, CNRS, UMR 5810, Lab Aminoacides Peptides & Prot, F-34095 Montpellier 5, France
[2] Univ Montpellier 2, CNRS, UMR 5810, Lab Aminoacides Peptides & Prot, F-34095 Montpellier, France
关键词
alpha-amino acid; asymmetric synthesis; chiral reagent; asymmetric auxiliary;
D O I
10.1007/BF01388170
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
Various methodologies published in the literature dealing with alpha-amino carboxylic acid asymmetric synthesis are presented in a digest form. In each case, only some recent or most typical works are mentioned.
引用
收藏
页码:215 / 250
页数:36
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共 133 条
[1]   Chemoenzymatic synthesis of a novel ligand for rhodium-catalysed asymmetric hydrogenation [J].
Adger, B ;
Berens, U ;
Griffiths, MJ ;
Kelly, MJ ;
McCague, R ;
Miller, JA ;
Palmer, CF ;
Roberts, SM ;
Selke, R ;
Vitinius, U ;
Ward, G .
CHEMICAL COMMUNICATIONS, 1997, (18) :1713-1714
[2]   OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ASPARTIC AND GLUTAMIC-ACID THROUGH DILITHIUM ENOLATOCARBOXYLATES OF 2-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]ACETIC AND 3-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]PROPIONIC ACID, RESPECTIVELY [J].
AEBI, JD ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1985, 68 (06) :1507-1518
[3]   DIASTEREOSELECTIVE RADICAL-ADDITION TO DERIVATIVES OF DEHYDROALANINE AND OF DEHYDROLACTIC ACID [J].
BECKWITH, ALJ ;
CHAI, CLL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) :1087-1088
[4]   CYCLIC-DERIVATIVES OF 3,3-DIPHENYLALANINE (DIP) (II), NOVEL ALPHA-AMINO-ACIDS FOR PEPTIDES OF BIOLOGICAL INTEREST [J].
BEYLIN, VG ;
CHEN, HG ;
DUNBAR, J ;
GOEL, OP ;
HARTER, W ;
MARLATT, M ;
TOPLISS, JG .
TETRAHEDRON LETTERS, 1993, 34 (06) :953-956
[5]   Sulfinimines of trifluoropyruvate:: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids [J].
Bravo, P ;
Crucianelli, M ;
Vergani, B ;
Zanda, M .
TETRAHEDRON LETTERS, 1998, 39 (42) :7771-7774
[6]   OBSERVATIONS ON SN-LI EXCHANGE IN ALPHA-AMINOORGANOSTANNANES AND THE CONFIGURATIONAL STABILITY OF NONSTABILIZED ALPHA-AMINOORGANOLITHIUMS [J].
BURCHAT, AF ;
CHONG, JM ;
PARK, SB .
TETRAHEDRON LETTERS, 1993, 34 (01) :51-54
[7]   ASYMMETRIC MICHAEL-ADDITIONS - STEREOSELECTIVE ALKYLATION OF CHIRAL, NON-RACEMIC ENOLATES BY NITROOLEFINS - PREPARATION OF ENANTIOMERICALLY PURE GAMMA-AMINOBUTYRIC AND SUCCINIC ACID-DERIVATIVES [J].
CALDERARI, G ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1985, 68 (06) :1592-1604
[8]   Asymmetric synthesis of alpha-amino acids via diastereoselective addition of (R)-pantolactone to their ketenes [J].
Calmes, M ;
Daunis, J ;
Mai, N .
TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1641-1648
[9]   Tertiary amines: a decisive factor in the stereoselective addition of (R)-pantolactone to N-phthalyl valine ketene [J].
Calmes, M ;
Daunis, J ;
Mai, N .
TETRAHEDRON, 1997, 53 (40) :13719-13726
[10]   ASYMMETRIC-SYNTHESIS OF FUNCTIONALIZED ALPHA-AMINO-BETA-HYDROXY ACIDS VIA CHIRAL NOREPHEDRINE-DERIVED OXAZOLIDINES [J].
CARDANI, S ;
BERNARDI, A ;
COLOMBO, L ;
GENNARI, C ;
SCOLASTICO, C ;
VENTURINI, I .
TETRAHEDRON, 1988, 44 (17) :5563-5572