A simplified synthesis of (+/-)-1,2-diphenyl-1,2-diaminoethane (1) from benzaldehyde and ammonia. Revision of the structures of the long-known intermediates ''hydrobenzamide'' and ''amarine''

被引:61
作者
Corey, EJ
Kuhnle, FNM
机构
[1] Dept. of Chem. and Chemical Biology, Harvard University, Cambridge
关键词
D O I
10.1016/S0040-4039(97)10372-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new pathway for the simple, stereocontrolled and economical synthesis of (+/-)-1 from benzaldehyde is described. The structures of two intermediates (Scheme 1) have been revised to those shown in Scheme 2. (C) 1997 Elsevier Science Ltd.
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页码:8631 / 8634
页数:4
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共 36 条
[1]  
[Anonymous], 1837, ANN PHARM
[2]  
BERTAGNINI C, 1853, LIEBIGS ANN CHEM, V88, P127
[3]   PREPARATION OF 1,2-DIARYLETHYLENEDIAMINES BY AMINATIVE REDUCTIVE COUPLING OF AROMATIC-ALDEHYDES WITH LOW-VALENT TITANIUM REAGENTS [J].
BETSCHART, C ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1987, 70 (08) :2215-2231
[4]   SCOPE AND LIMITATIONS OF THE REDUCTIVE COUPLING OF AROMATIC ALDIMINE DERIVATIVES WITH FORMATION OF 1,2-DIARYLETHYLENEDIAMINE UNITS, USING LOW-VALENT TITANIUM REAGENTS [J].
BETSCHART, C ;
SCHMIDT, B ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1988, 71 (08) :1999-2021
[5]   ASYMMETRIC CATALYSIS .18. ENANTIOSELECTIVE MICHAEL ADDITIONS WITH OPTICALLY-ACTIVE COII/DIAMINE CATALYSTS [J].
BRUNNER, H ;
HAMMER, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (04) :312-313
[6]   X-ray crystal and NMR structure of a highly reactive bidentate 1,2-diamine-OsO4 complex, formally a 20-electron outer valence shell species. Mechanistic implications for the 1,2-diamine-accelerated dihydroxylation of olefins by OsO4 [J].
Corey, EJ ;
Sarshar, S ;
Azimioara, MD ;
Newbold, RC ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (33) :7851-7852
[7]   A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS [J].
COREY, EJ ;
YU, CM ;
LEE, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :878-879
[8]   PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].
COREY, EJ ;
IMWINKELRIED, R ;
PIKUL, S ;
XIANG, YB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495
[9]   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
[10]   ENANTIOSELECTIVE SYNTHESIS OF THE C(18)-C(35) SEGMENT OF IMMUNOSUPPRESSANT FK-506 USING EFFICIENT NEW METHODOLOGY [J].
COREY, EJ ;
HUANG, HC .
TETRAHEDRON LETTERS, 1989, 30 (39) :5235-5238