Novel Mg-organic reagents in organic synthesis. Cp2TiCl2 catalyzed intermolecular cyclomagnesiation of cyclic and acyclic 1,2-dienes using Grignard reagents

被引：44

作者：

D'yakonov, Vladimir A. ^{[1
]}

Makarov, Aleksey A. ^{[1
]}

Ibragimov, Askhat G. ^{[1
]}

Khalilov, Leonard M. ^{[1
]}

Dzhemilev, Usein M. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Petrochem & Catalysis, Ufa 450075, Russia

来源：

TETRAHEDRON | 2008年 / 64卷 / 44期

关键词：

Metallacycles; Cyclomagnesiation; Allenes; Homogeneous catalysis; Titanium; Dzhemilev reaction;

D O I：

10.1016/j.tet.2008.08.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High-yield (> 80%) catalytic intermolecular cyclomagnesiation of cyclic and acyclic allenes with the aid of Grignard reagents has been realized in the presence of Cp2TiCl2. The synthesized unsaturated bi- and tricyclic organomagnesium compounds (OMC) have been successfully converted in situ into thiophenes, unsaturated ketones, cyclic and acyclic hydrocarbons with high regio- and stereoselectivity. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10188 / 10194

页数：7

共 7 条

[1] Cyclomagnesiation of nitrogen-containing 1,2-dienes with grignard compounds catalyzed by Cp2TiCl2
V. A. D’yakonov
A. A. Makarov
E. Kh. Makarova
L. M. Khalilov
U. M. Dzhemilev
Russian Journal of Organic Chemistry, 2012, 48 : 349 - 353
[2] Cyclomagnesiation of Nitrogen-Containing 1,2-Dienes with Grignard Compounds Catalyzed by Cp2TiCl2
D'yakonov, V. A.
Makarov, A. A.
Makarova, E. Kh.
Khalilov, L. M.
Dzhemilev, U. M.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (03) : 349 - 353
[3] Synthesis and transformations of metallacycles 41.☆ Cyclomagnesiation of O-containing 1,2-dienes with Grignard reagents in the presence of Cp2TiCl2
D'yakonov, V. A.
Makarov, A. A.
Makarova, E. Kh.
Khalilov, L. M.
Dzhemilev, U. M.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (10) : 1943 - 1949
[4] Synthesis and transformations of metallacycles 41. Cyclomagnesiation of O-containing 1,2-dienes with Grignard reagents in the presence of Cp2TiCl2
V. A. D’yakonov
A. A. Makarov
E. Kh. Makarova
L. M. Khalilov
U. M. Dzhemilev
Russian Chemical Bulletin, 2012, 61 : 1943 - 1949
[5] NOVEL REACTIONS OF LOW VALENT TITANIUM AND ZIRCONIUM REAGENTS GENERATED BY REDUCTION OF CP2TICL2 AND CP2ZRCL2 WITH MAGNESIUM AND 1,2-DIBROMOETHANE
RAO, SA
PERIASAMY, M
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 352 (1-2) : 125 - 131
[6] CP2TICL2-CATALYZED GRIGNARD EXCHANGE-REACTIONS WITH 1,3-DIENES OR STYRENES - PREPARATION OF ALLYLIC AND ALPHA-ARYLETHYL GRIGNARD-REAGENTS BY A CONVENIENT AND QUANTITATIVE METHOD
SATO, F
ISHIKAWA, H
SATO, M
TETRAHEDRON LETTERS, 1980, 21 (04) : 365 - 368
[7] ENZYMES AS REAGENTS IN ORGANIC-CHEMISTRY - TRANSKETOLASE-CATALYZED SYNTHESIS OF D-[1,2-(C-13)2]XYLULOSE
DEMUYNCK, C
BOLTE, J
HECQUET, L
SAMAKI, H
CARBOHYDRATE RESEARCH, 1990, 206 (01) : 79 - 85

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