Metallation of benzylic amines via amine-borane complexes

被引：31

作者：

Ebden, MR

Simpkins, NS

Fox, DNA

机构：

[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England

[2] Pfizer Ltd, Cent Res, Dept Discovery Chem, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON | 1998年 / 54卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(98)00783-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formation of borane complexes of N,N-dimeihylbenzylamine, N,N-dimethyl(1-naphthyl)methylamine, N,N-dimethyl(2-naphthyl)methylamine, N -methyltetrahydroisoquinoline and N-methylisoindoline facilitates regioselective metallation of these systems using BuLi, giving intermediate benzylic anions which react with a range of electrophiles to give products in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：12923 / 12952

页数：30

相关论文

共 33 条

[1] TETRAHYDROISOQUINOLINES .3. STEREOSELECTIVE SYNTHESIS OF CIS- AND TRANS-1,4-DISUBSTITUTED N-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINES AS THEIR TRICARBONYLCHROMIUM COMPLEXES [J].

BLAGG, J ;

COOTE, SJ ;

DAVIES, SG ;

MIDDLEMISS, D ;

NAYLOR, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :689-694

[2]

Blake AJ, 1998, SYNLETT, P189

[3] NEW METHODS FOR CREATING SILICON-CARBON BOND FROM CHLOROSILANES .9. SILYLATION OF AROMATIC AMIDES [J].

BOURGEOIS, P ;

CALAS, R ;

DUFFAUT, N ;

DUNOGUES, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 32 (01) :79-+

[4]

BRAUN JV, 1904, BERICHTE, V37, P2678

[5] SELECTIVE REDUCTIONS .29. A SIMPLE TECHNIQUE TO ACHIEVE AND ENHANCED RATE OF REDUCTION OF REPRESENTATIVE ORGANIC-COMPOUNDS BY BORANE-DIMETHYL SULFIDE [J].

BROWN, HC ;

CHOI, YM ;

NARASIMHAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3153-3163

[6] SELECTIVE REDUCTIONS .18. FAST REACTION OF PRIMARY, SECONDARY, AND TERTIARY AMIDES WITH DIBORANE - SIMPLE, CONVENIENT PROCEDURE FOR CONVERSION OF AMIDES TO CORRESPONDING AMINES [J].

BROWN, HC ;

HEIM, P .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (05) :912-916

[7] SELECTIVE REDUCTIONS .V. PARTIAL RED1CTION OF TERTIARY AMIDES BY LITHIUM DI- + TRIETHOXYALUMINOHYDRIDES-NEW ALDEHYDE SYNTHESIS VIA DIMETHYLAMIDES [J].

BROWN, HC ;

TSUKAMOTO, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) :1089-&

[8] SOMMELET-HAUSER REARRANGEMENT OF ALLYLBENZYLDIMETHYLAMMONIUM BROMIDE AND CYCLOPROPYLCARBINYLBENZYLDIMETHYLAMMONIUM BROMIDE - EVIDENCE FOR CARBANION STABILIZATION BY CYCLOPROPANE RING [J].

BUMGARDNER, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (01) :73-&

[9]

DECOSTA BR, 1992, SYNTHESIS-STUTTGART, P887

[10]

DUNN DL, 1934, J CHEM SOC, P279

← 1 2 3 4 →