Enantioselective solid-phase synthesis of α-amino acid derivatives

被引:95
作者
O'Donnell, MJ [1 ]
Delgado, F [1 ]
Pottorf, RS [1 ]
机构
[1] Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA
关键词
amino acids and derivatives; enantiocontrol; phase transfer; solid-phase synthesis;
D O I
10.1016/S0040-4020(99)00211-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Wang-resin bound derivatives of glycine Schiff base esters are alkylated in the presence of quaternary ammonium salts derived from cinchonidine or cinchonine using phosphazene bases to give either enantiomer of the product a-amino acid derivatives in 51-89% ee. (C) 1999 Elsevier Science Ltd. All rights reserved. Keywords: Amino acids and derivatives, Enantiocontrol, Phase transfer, Solid-phase synthesis.
引用
收藏
页码:6347 / 6362
页数:16
相关论文
共 70 条
[1]   Peptide and peptidomimetic libraries - Molecular diversity and drug design [J].
Al-Obeidi, E ;
Hruby, VJ ;
Sawyer, TK .
MOLECULAR BIOTECHNOLOGY, 1998, 9 (03) :205-223
[2]  
Annis DA, 1998, ANGEW CHEM INT EDIT, V37, P1907, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1907::AID-ANIE1907>3.0.CO
[3]  
2-A
[4]   Rapid solid phase synthesis of α-amino acids [J].
Barbaste, M ;
Rolland-Fulcrand, V ;
Roumestant, ML ;
Viallefont, P ;
Martinez, J .
TETRAHEDRON LETTERS, 1998, 39 (35) :6287-6290
[5]   Applications of solid-supported organic synthesis in combinatorial chemistry - Preface [J].
Bristol, JA .
TETRAHEDRON, 1997, 53 (19) :R13-R13
[6]  
Brown AR, 1998, SYNLETT, P817
[7]  
Brown RCD, 1998, J CHEM SOC PERK T 1, P3293
[8]  
BUNIN BA, 1998, COMBINATORIAL INDEX
[9]   Asymmetric synthesis of (S)-α-methyl α-amino acids by alkylation of chiral 3,6-dihydro-2H-1,4-oxazin-2-ones using unactivated alkyl halides and organic bases [J].
Chinchilla, R ;
Galindo, N ;
Nájera, C .
TETRAHEDRON-ASYMMETRY, 1998, 9 (16) :2769-2772
[10]   Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst [J].
Corey, EJ ;
Noe, MC ;
Xu, F .
TETRAHEDRON LETTERS, 1998, 39 (30) :5347-5350