SIMPLE SYNTHESIS OF A C-2 SYMMETRICAL VICINAL DIAMINE - HIGHLY DIASTEREOSELECTIVE GRIGNARD ADDITION TO A CHIRAL BIS-IMINE

被引：95

作者：

BAMBRIDGE, K ^{[1
]}

BEGLEY, MJ ^{[1
]}

SIMPKINS, NS ^{[1
]}

机构：

[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(00)76916-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the enantiomerically pure bis-imine derived from glyoxal and (R)-alpha-methylbenzylamine with PhMgCl in diethylether is highly diastereoselective, resulting in the selective formation of the C-2 symmetric vicinal diamine 7.

引用

页码：3391 / 3394

页数：4

共 17 条

[11] THE STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED VICINAL DIAMINE SYSTEMS BY THE DOUBLE ALLYLATION REACTIONS OF PROTECTED 1,2-BISIMINE PRECURSORS [J].

NEUMANN, WL ;

ROGIC, MM ;

DUNN, TJ .

TETRAHEDRON LETTERS, 1991, 32 (42) :5865-5868

[12] STEREOSPECIFIC CONVERSION OF CHIRAL 1,2-CYCLIC SULFATES TO CHIRAL IMIDAZOLINES [J].

OI, R ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1991, 32 (08) :999-1002

[13] STEREOSELECTIVE SYNTHESIS OF VICINAL DIAMINES [J].

REETZ, MT ;

JAEGER, R ;

DREWLIES, R ;

HUBEL, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (01) :103-106

[14] CRYSTALLOGRAPHIC AND LI-6 AND N-15 NMR-STUDIES OF A CHIRAL BIDENTATE LITHIUM AMIDE - AN EFFECT OF AGGREGATION STATES ON AN ENANTIOSELECTIVE DEPROTONATION REACTION [J].

SATO, D ;

KAWASAKI, H ;

SHIMADA, I ;

ARATA, Y ;

OKAMURA, K ;

DATE, T ;

KOGA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :761-763

[15]

TOMIOKA K, 1990, SYNTHESIS-STUTTGART, P541

[16] C2 SYMMETRY AND ASYMMETRIC INDUCTION [J].

WHITESELL, JK .

CHEMICAL REVIEWS, 1989, 89 (07) :1581-1590

[17] STUDIES ON THE REACTION OF ALPHA-IMINO ESTERS WITH ORGANOMETALLIC COMPOUNDS [J].

YAMAMOTO, Y ;

ITO, W .

TETRAHEDRON, 1988, 44 (17) :5415-5423

← 1 2 →