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：60

作者：

Corey, EJ

Kuhnle, FNM

机构：

[1] Dept. of Chem. and Chemical Biology, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 50期

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.

引用

页码：8631 / 8634

页数：4

共 36 条

[11] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES
COREY, EJ
YU, CM
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5495 - 5496
[12] ENANTIOSELECTIVE TOTAL SYNTHESIS OF GRACILIN-B AND GRACILIN-C USING CATALYTIC ASYMMETRIC DIELS-ALDER METHODOLOGY
COREY, EJ
LETAVIC, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (37) : 9616 - 9617
[13] ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL
COREY, EJ
JARDINE, PD
VIRGIL, S
YUEN, PW
CONNELL, RD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) : 9243 - 9244
[14] CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF A KEY INTERMEDIATE FOR THE SYNTHESIS OF PROSTANOIDS
COREY, EJ
IMAI, N
PIKUL, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (51) : 7517 - 7520
[15] FIRST EXAMPLE OF A HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER REACTION OF AN ACHIRAL C-2-NU-SYMMETRICAL DIENOPHILE AND AN ACHIRAL DIENE
COREY, EJ
SARSHAR, S
LEE, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 12089 - 12090
[16] X-RAY CRYSTALLOGRAPHIC AND NMR-STUDIES ON THE ORIGINS OF HIGH ENANTIOSELECTIVITY IN DIELS-ALDER REACTIONS CATALYZED BY A CHIRAL DIAZAALUMINOLIDINE
COREY, EJ
SARSHAR, S
BORDNER, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) : 7938 - 7939
[17] VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS
COREY, EJ
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) : 4976 - 4977
[18] COREY EJ, 1989, P 31 NAT ORG CHEM S, P1
[19] Chiral magnesium bis(sulfonamide) complexes as catalysts for the merged enolization and enantioselective amination of N-acyloxazolidinones. A catalytic approach to the synthesis of arylglycines
Evans, DA
Nelson, SG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) : 6452 - 6453
[20] AMINOPHOSPHINE-RHODIUM COMPLEXES AS CATALYSTS IN ASYMMETRIC HYDROGENATION - DEPENDENCE OF THE ENANTIOSELECTIVITY ON THE STRUCTURE OF THE CHIRAL LIGANDS
FIORINI, M
GIONGO, GM
[J]. JOURNAL OF MOLECULAR CATALYSIS, 1979, 5 (04): : 303 - 310

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