Parallel synthesis of homochiral β-amino acids

被引:45
作者
Davies, Stephen G. [1 ]
Mulvaney, Andrew W. [1 ]
Russell, Angela J. [1 ]
Smith, Andrew D. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Dept Organ Chem, Oxford OX1 3TA, England
基金
英国生物技术与生命科学研究理事会;
关键词
D O I
10.1016/j.tetasy.2007.06.008
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The parallel asymmetric synthesis of an array of 30 P-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 alpha,beta-unsaturated esters to both enantiomeric series of the corresponding beta-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1554 / 1566
页数:13
相关论文
共 62 条
[1]  
ACHIWA K, 1987, TETRAHEDRON LETT, V28, P1119
[2]   Enantioselective synthesis of α,β-substituted β-amino acids [J].
Agami, C ;
Cheramy, S ;
Dechoux, L ;
Melaimi, E .
TETRAHEDRON, 2001, 57 (01) :195-200
[3]   Residue-based control of helix shape in beta-peptide oligomers [J].
Appella, DH ;
Christianson, LA ;
Klein, DA ;
Powell, DR ;
Huang, XL ;
Barchi, JJ ;
Gellman, SH .
NATURE, 1997, 387 (6631) :381-384
[4]  
BAKER M, Patent No. 107112
[5]   Chemical synthesis of a glycolipid library by a solid-phase strategy allows elucidation of the structural specificity of immunostimulation by rhamnolipids [J].
Bauer, Joerg ;
Brandenburg, Klaus ;
Zaehringer, Ulrich ;
Rademann, Joerg .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (27) :7116-7124
[6]   STEREOSELECTIVE PREPARATION OF BETA-AMINO-ACYL IRON COMPLEXES FOR BETA-LACTAM SYNTHESIS [J].
BROADLEY, K ;
DAVIES, SG .
TETRAHEDRON LETTERS, 1984, 25 (16) :1743-1744
[7]   CONTRIBUTION TO ASYMMETRIC SYNTHESIS OF BICYCLIC COMPOUNDS CATALYZED BY OPTICALLY-ACTIVE AMINO-ACIDS - SYNTHESIS OF (S)-2-PYRROLIDINEPROPIONIC ACID AND (R)-4-AMINO-5-PHENYLVALERIC ACID [J].
BUCHSCHACHER, P ;
CASSAL, JM ;
FURST, A ;
MEIER, W .
HELVETICA CHIMICA ACTA, 1977, 60 (08) :2747-2755
[8]   Two- and three dimensional combinatorial chemistry from multicomponent Grignard reagents [J].
Bülow, A ;
Sinning, S ;
Wiborg, O ;
Bols, M .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (04) :509-519
[9]   ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID [J].
BUNNAGE, ME ;
BURKE, AJ ;
DAVIES, SG ;
GOODWIN, CJ .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :165-176
[10]   INTRAMOLECULAR HYDROGEN-BONDING IN DERIVATIVES OF BETA-ALANINE AND GAMMA-AMINO BUTYRIC-ACID - MODEL STUDIES FOR THE FOLDING OF UNNATURAL POLYPEPTIDE BACKBONES [J].
DADO, GP ;
GELLMAN, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1054-1062