Deracemization of (+/-)-2,2-disubstituted epoxides via enantioconvergent chemoenzymatic hydrolysis using Nocardia EH1 epoxide hydrolase and sulfuric acid

被引:29
作者
Orru, RVA [1 ]
Kroutil, W [1 ]
Faber, K [1 ]
机构
[1] GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA
基金
奥地利科学基金会;
关键词
D O I
10.1016/S0040-4039(97)00201-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Substituted (S)-1,2-diols were prepared in a one-pot procedure with >90% ee and >90% isolated yield via deracemization of (+/-)-2,2-disubstituted oxiranes through sequential (i) biocatalytic asymmetric hydrolysis using Nocardia EH1 epoxide hydrolase and (ii) acid catalyzed hydrolysis of the remaining oxirane enantiomer. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1753 / 1754
页数:2
相关论文
共 9 条
[1]   Chemoenzymic resolution and deracemisation of (+/-)-1-methyl-1,2-epoxycyclohexane: The synthesis of(1-S,2-S)-1-methylcyclohexane-1,2-diol. [J].
Archer, IVJ ;
Leak, DJ ;
Widdowson, DA .
TETRAHEDRON LETTERS, 1996, 37 (48) :8819-8822
[2]   MECHANISM OF ACID-CATALYSED ALCOHOLYSIS OF EPOXIDES .1. REACTIONS OF SUBSTITUTED (1,2-EPOXYETHYL)BENZENES [J].
BIGGS, J ;
CHAPMAN, NB ;
FINCH, AF ;
WRAY, V .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (01) :55-&
[3]   Microbial epoxide hydrolases [J].
Faber, K ;
Mischitz, M ;
Kroutil, W .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (03) :249-258
[4]   Regioselectivity of Rhodococcus NCIMB 11216 epoxide hydrolase: Applicability of E-values for description of enantioselectivity depends on substrate structure [J].
Mischitz, M ;
Mirtl, C ;
Saf, R ;
Faber, K .
TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :2041-2046
[5]   ASYMMETRIC MICROBIAL HYDROLYSIS OF EPOXIDES [J].
MISCHITZ, M ;
KROUTIL, W ;
WANDEL, U ;
FABER, K .
TETRAHEDRON-ASYMMETRY, 1995, 6 (06) :1261-1272
[6]  
OSPRIAN I, 1997, TETRAHEDRON-ASYMMETR, V8, P1
[7]   Microbiological transformations .32. Use of epoxide hydrolase mediated biohydrolysis as a way to enantiopure epoxides and vicinal diols: Application to substituted styrene oxide derivatives. [J].
PedragosaMoreau, S ;
Archelas, A ;
Furstoss, R .
TETRAHEDRON, 1996, 52 (13) :4593-4606
[8]  
STECHER H, 1997, IN PRESS SYNTHESIS
[9]   COMBINATION OF THE LIPASE-CATALYZED RESOLUTION WITH THE MITSUNOBU ESTERIFICATION IN ONE-POT [J].
VANTTINEN, E ;
KANERVA, LT .
TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1779-1786