Dynamic kinetic resolution:: synthesis of optically active α-amino acid derivatives

被引:60
作者
Brown, SA
Parker, MC
Turner, NJ
机构
[1] Univ Edinburgh, Dept Chem, Edinburgh Ctr Prot Technol, Edinburgh EH9 3JJ, Midlothian, Scotland
[2] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland
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/S0957-4166(00)00108-7
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
Candida antarctica lipase B (Novozyme) is an effective catalyst for the dynamic kinetic resolution of racemic 2-benzyl-4-substituted-5(4H)-oxazolones, in the presence of an alcohol, yielding optically active N-benzoyl amino acid esters. The reaction has been optimised with respect to the solvent and the effect of a catalytic amount of organic base is investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1687 / 1690
页数:4
相关论文
共 13 条
[1]
ENZYMATIC-SYNTHESIS OF OPTICALLY-ACTIVE AMINO-ACIDS - EFFECT OF SOLVENT ON THE ENANTIOSELECTIVITY OF LIPASE-CATALYZED RING-OPENING OF OXAZOLIN-5-ONES [J].
BEVINAKATTI, HS ;
BANERJI, AA ;
NEWADKAR, RV ;
MOKASHI, AA .
TETRAHEDRON-ASYMMETRY, 1992, 3 (12) :1505-1508
[2]
LIPASE-CATALYZED ENANTIOSELECTIVE RING-OPENING OF OXAZOL-5(4H)-ONES COUPLED WITH PARTIAL INSITU RACEMIZATION OF THE LESS REACTIVE ISOMER [J].
BEVINAKATTI, HS ;
NEWADKAR, RV ;
BANERJI, AA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) :1091-1092
[3]
Dynamic resolutions in asymmetric synthesis [J].
Caddick, S ;
Jenkins, K .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (06) :447-&
[4]
ENZYMATIC ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ENANTIOSELECTIVE CLEAVAGE OF 4-SUBSTITUTED OXAZOLIN-5-ONES AND THIAZOLIN-5-ONES [J].
CRICH, JZ ;
BRIEVA, R ;
MARQUART, P ;
GU, RL ;
FLEMMING, S ;
SIH, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3252-3258
[5]
ON SPONTANEOUS AND ENZYME-CATALYZED HYDROLYSIS OF SATURATED OXAZOLINONES [J].
DEJERSEY, J ;
ZERNER, B .
BIOCHEMISTRY, 1969, 8 (05) :1967-&
[6]
FABER K, 1995, BIOTRANSFORMATIONS O, P80
[7]
CHEMOENZYMATIC ASYMMETRIC-SYNTHESIS OF AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYZES OF 2-PHENYL-OXAZOLIN-5-ONES [J].
GU, RL ;
LEE, IS ;
SIH, CJ .
TETRAHEDRON LETTERS, 1992, 33 (15) :1953-1956
[8]
Lipase-catalyzed chemoselective N-acylation of amino-sugar derivatives in hydrophobic solvent: Acid-amine ion-pair effects. [J].
Maugard, T ;
RemaudSimeon, M ;
Petre, D ;
Monsan, P .
TETRAHEDRON, 1997, 53 (22) :7587-7594
[9]
STEREOSELECTIVE ORGANIC-SYNTHESIS VIA DYNAMIC KINETIC RESOLUTION [J].
NOYORI, R ;
TOKUNAGA, M ;
KITAMURA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (01) :36-55
[10]
Enhancement of Candida antarctica lipase B enantioselectivity and activity in organic solvents [J].
Parker, MC ;
Brown, SA ;
Robertson, L ;
Turner, NJ .
CHEMICAL COMMUNICATIONS, 1998, (20) :2247-2248