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
[1]   DERACEMIZATION OF SILYL ENOL ETHERS [J].
CAVELIER, F ;
GOMEZ, S ;
JACQUIER, R ;
VERDUCCI, J .
TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2501-2505
[2]   A FIRST APPROACH TO ASYMMETRIC PROTONATION VIA A POLYMER-SUPPORTED CHIRAL PROTON DONOR [J].
CAVELIER, F ;
GOMEZ, S ;
JACQUIER, R ;
VERDUCCI, J .
TETRAHEDRON LETTERS, 1994, 35 (18) :2891-2894
[3]   HYDROCHLORIDE OF CHIRAL PIPERAZINE AS A CHIRAL PROTON SOURCE [J].
FUJI, K ;
TANAKA, K ;
MIYAMOTO, H .
TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :247-259
[4]   ENANTIOSELECTIVE PROTONATION OF ENOLATES - NOVEL CHIRAL PROTON SOURCES AND REMARKABLE EFFECTS OF THE COUNTERCATION [J].
FUJI, K ;
KAWABATA, T ;
KURODA, A ;
TAGA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :1914-1915
[5]   ENANTIOFACIAL PROTONATION BY CATALYTIC ANTIBODIES [J].
FUJII, I ;
LERNER, RA ;
JANDA, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8528-8529
[6]   HYDROXYLATION OF PIPERITONE BY CELL-SUSPENSION CULTURES OF CATHARANTHUS-ROSEUS [J].
HAMADA, H ;
FUCHIKAMI, Y ;
IKEMATSU, Y ;
HIRATA, T ;
WILLIAMS, HJ ;
SCOTT, AI .
PHYTOCHEMISTRY, 1994, 37 (04) :1037-1038
[7]   PALLADIUM-CATALYZED CLEAVAGE OF PROCHIRAL ENOL CARBONATES - ENANTIOSELECTIVE KETONIZATION OF RESULTING ENOLS [J].
HENIN, F ;
MUZART, J .
TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1161-1164
[8]   THE BIOTRANSFORMATION OF FOREIGN SUBSTRATES BY TISSUE-CULTURES .1. THE HYDROXYLATION OF LINALOOL AND ITS RELATED-COMPOUNDS WITH THE SUSPENSION CELLS OF NICOTIANA-TABACUM [J].
HIRATA, T ;
AOKI, T ;
HIRANO, Y ;
ITO, T ;
SUGA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (11) :3527-3529
[9]   Asymmetric hydrogenation of the C-C double bond of enones with the reductases from Nicotiana tabacum [J].
Hirata, T ;
Shimoda, K ;
Gondai, T .
CHEMISTRY LETTERS, 2000, (08) :850-851
[10]   LEWIS-ACID ASSISTED CHIRAL BRONSTED ACID FOR ENANTIOSELECTIVE PROTONATION OF SILYL ENOL ETHERS AND KETENE BIS(TRIALKYLSILYL) ACETALS [J].
ISHIHARA, K ;
KANEEDA, M ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11179-11180