ASYMMETRIC REDUCTION OF A CARBON-NITROGEN DOUBLE-BOND - ENANTIOSELECTIVE SYNTHESIS OF 4,5-DIHYDRO-3H-2,3-BENZODIAZEPINES

被引:23
作者
LING, I
PODANYI, B
HAMORI, T
SOLYOM, S
机构
[1] Institute for Drug Research Ltd., H-1325 Budapest
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 11期
关键词
D O I
10.1039/p19950001423
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly specific enantioselective reduction, elaborated for the reduction of the 3,4-carbon-nitrogen double bond of 4-methyl-7,8-methylenedioxy-1-(4-nitrophenyl)-4,5-dihydro-3H-2,3-benzodiazepine 4 made possible the synthesis of the enantiomers of the potent non-competitive AMPA/kainate antagonists 2a, b. NMR Investigations of the reducing complex show that there is no formation of an 1,3,2-oxazaborolidine ring as may have been presumed on the basis of literature data.
引用
收藏
页码:1423 / 1427
页数:5
相关论文
共 32 条
[1]  
ANDRASI F, Patent No. 0492485
[2]   ASYMMETRIC REDUCTION OF 7,8-DIFLUORO-3-METHYL-2H-1,4-BENZOXAZINE - SYNTHESIS OF A KEY INTERMEDIATE OF (S)-(-)-OFLOXACIN (DR-3355) [J].
ATARASHI, S ;
TSURUMI, H ;
FUJIWARA, T ;
HAYAKAWA, I .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (02) :329-331
[3]   ASYMMETRIC CATALYZES .28. ENANTIOSELECTIVE HYDROSILYLATION OF PROCHIRAL 3,4-DIHYDRO-2H-PYRROLE DERIVATIVES [J].
BECKER, R ;
BRUNNER, H ;
MAHBOOBI, S ;
WIEGREBE, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (11) :995-996
[4]   ASYMMETRIC HYDROGENATION OF A CARBON-NITROGEN DOUBLE-BOND IN FOLIC-ACID [J].
BOYLE, PH ;
KEATING, MT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (10) :375-376
[5]   ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE METOLACHLOR VIA ASYMMETRIC REDUCTION [J].
CHO, BT ;
CHUN, YS .
TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :337-340
[6]   ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE SECONDARY-AMINES VIA ASYMMETRIC REDUCTION [J].
CHO, BT ;
CHUN, YS .
TETRAHEDRON-ASYMMETRY, 1992, 3 (12) :1583-1590
[7]   ASYMMETRIC REDUCTION OF N-SUBSTITUTED KETIMINES WITH THE REAGENT PREPARED FROM BORANE AND (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL (ITSUNOS REAGENT) - ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE SECONDARY-AMINES [J].
CHO, BT ;
CHUN, YS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3200-3201
[8]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[9]  
DELAIR P, 1994, J ORG CHEM, V59, P4684
[10]  
GAWLEY RE, 1989, HETEROCYCLES, V29, P1283