Asymmetric hydrogenation of N-substituted maleimides by cultured plant cells

被引:15
作者
Hirata, T
Takarada, A
Matsushima, A
Kondo, Y
Hamada, H
机构
[1] Hiroshima Univ, Grad Sch Sci, Dept Math & Life Sci, Higashihiroshima 7398526, Japan
[2] Hiroshima Univ, Nat Sci Ctr Basic Res & Dev, Higashihiroshima 7398526, Japan
[3] Okayama Univ Sci, Dept Appl Sci, Okayama 7000005, Japan
关键词
D O I
10.1016/j.tetasy.2003.10.033
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The cultured suspension cells of higher plants hydrogenated the C-C double bond of N-substituted maleimides to afford the corresponding succinimides. Hydrogenation of N-phenyl-2-methylmaleimide by the cultured cells of Nicotiana tabacum proved to be highly enantioselective and gave (R)-N-phenyl-2-methylsuccinimide (99% ee). (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:15 / 16
页数:2
相关论文
共 18 条
[11]   Old Yellow Enzyme from Candida macedoniensis catalyzes the stereospecific reduction of the C=Cbond of ketoisophorone [J].
Kataoka, M ;
Kotaka, A ;
Hasegawa, A ;
Wada, M ;
Yoshizumi, A ;
Nakamori, S ;
Shimizu, S .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2002, 66 (12) :2651-2657
[12]   ENZYME-MEDIATED ENANTIOFACE-DIFFERENTIATING HYDROLYSIS OF ALPHA-SUBSTITUTED CYCLOALKANONE ENOL ESTERS [J].
MATSUMOTO, K ;
TSUTSUMI, S ;
IHORI, T ;
OHTA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9614-9619
[13]   A REVISED MEDIUM FOR RAPID GROWTH AND BIO ASSAYS WITH TOBACCO TISSUE CULTURES [J].
MURASHIGE, T ;
SKOOG, F .
PHYSIOLOGIA PLANTARUM, 1962, 15 (03) :473-497
[14]   ENANTIOSELECTIVE AND DIASTEREOSELECTIVE PROTONATION OF PHOTODIENOLS - TOTAL SYNTHESIS OF (R)-(-)-LAVANDULOL [J].
PIVA, O .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7879-7883
[15]   MEDIUM AND TECHNIQUES FOR INDUCTION AND GROWTH OF MONOCOTYLEDONOUS AND DICOTYLEDONOUS PLANT-CELL CULTURES [J].
SCHENK, RU ;
HILDEBRANDT, AC .
CANADIAN JOURNAL OF BOTANY, 1972, 50 (01) :199-+
[16]   A novel reductase participating in the hydrogenation of an exocyclic C-C double bond of enones from Nicotiana tabacum [J].
Shimoda, K ;
Izumi, S ;
Hirata, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (04) :813-816
[17]   The first example of enantioselective protonation of prochiral enolates with chiral gamma-hydroxyselenoxides [J].
Takahashi, T ;
Nakao, N ;
Koizumi, T .
CHEMISTRY LETTERS, 1996, (03) :207-208
[18]   ENANTIOSELECTIVE PROTONATION OF ACHIRAL LITHIUM ENOLATES USING A CHIRAL AMINE IN THE PRESENCE OF LITHIUM BROMIDE [J].
YASUKATA, T ;
KOGA, K .
TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :35-38