STEREOCONTROL IN THE REDUCTION OF 1,2-DIIMINE WITH AN OXAZABOROLIDINE CATALYST - HIGHLY STEREOSELECTIVE PREPARATION OF (R,R)-1,2-DIPHENYLETHYLENEDIAMINE

被引：62

作者：

SHIMIZU, M ^{[1
]}

KAMEI, M ^{[1
]}

FUJISAWA, T ^{[1
]}

机构：

[1] MIE UNIV,DEPT CHEM MAT,TSU,MIE 514,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 47期

关键词：

D O I：

10.1016/0040-4039(95)01825-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioselective reduction of 1,2-bis(p-methoxyphenylimino)-1,2-diphenylethane was conducted even with 0.5 mol% of new oxazaborolidine derived form L-threonine and a stoichiometric amount of BH3 . THF to give 1,2-diphenylethylenediamine derivative in excellent enantiomeric purity. The subsequent deprotection of nitrogen atoms afforded (RP)-1,2-diphenylethylenediamine in enantiomerically pure form.

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页码：8607 / 8610

页数：4

相关论文

共 30 条

[1]

BOLM C, 1994, SYNLETT, P655

[2]

CHAN YNC, 1990, J AM CHEM SOC, V112, P9400

[3] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE METOLACHLOR VIA ASYMMETRIC REDUCTION [J].

CHO, BT ;

CHUN, YS .

TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :337-340

[4] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE SECONDARY-AMINES VIA ASYMMETRIC REDUCTION [J].

CHO, BT ;

CHUN, YS .

TETRAHEDRON-ASYMMETRY, 1992, 3 (12) :1583-1590

[5] 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

[6] TOTAL SYNTHESIS OF (+/-)-FORSKOLIN [J].

COREY, EJ ;

JARDINE, PD ;

ROHLOFF, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3672-3673

[7] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[8] CONVENIENT ROUTES TO SYMMETRICAL BENZILS AND CHIRAL 1,2-DIARYL-1,2-DIAMINOETHANES, USEFUL CONTROLLERS AND PROBES FOR ENANTIOSELECTIVE SYNTHESIS [J].

COREY, EJ ;

LEE, DH ;

SARSHAR, S .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :3-6

[9] 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

[10] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926