A major breakthrough in the use of alkoxycarbene complexes of chromium and tungsten for the synthesis of elaborate organic compounds:: Dihydropyridine induced reductions and cascade insertion reactions

被引：33

作者：

Rudler, H

Parlier, A

Durand-Réville, T

Martin-Vaca, B

Audouin, M

Garrier, E

Certal, V

Vaissermann, J

机构：

[1] Univ Paris 06, UMR 7611, Lab Synth Organ & Organomet, F-75252 Paris 5, France

[2] Univ Paris 06, ESA 7071, Lab Chim Inorgan & Mat Mol, F-75252 Paris, France

来源：

TETRAHEDRON | 2000年 / 56卷 / 28期

关键词：

tungsten; chromium; ylids; insertion reactions;

D O I：

10.1016/S0040-4020(00)00214-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkoxy (alkyl)carbene complexes of tungsten and chromium react with dihydropyridine and N-methyldihydropyridine to give respectively pyridinium ylid complexes and N-methylpyridinium tungstates and chromates. These two types of complexes can be used, for the former, as cyclopropanation reagents, for the latter, as unprecedented initiators of cascade multiinsertions of olefins, alkynes and CO. These insertions lead to elaborate polycyclic compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5001 / 5027

页数：27

相关论文

共 64 条

[1] KETENE ALKYLTRIALKYLSILYL ACETALS - SYNTHESIS, PRYOLYSIS AND NMR STUDIES [J].

AINSWORTH, C ;

CHEN, F ;

KUO, YN .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 46 (01) :59-+

[2]

ALPER H, 1978, J CHEM SOC CHEM COMM, V311

[3] BIDENTATE ALKENE CARBENE COMPLEXES OF TUNGSTEN - SYNTHESIS, STRUCTURE, AND REACTIVITY TOWARD ALKENES [J].

ALVAREZ, C ;

PACREAU, A ;

PARLIER, A ;

RUDLER, H .

ORGANOMETALLICS, 1987, 6 (05) :1057-1064

[4]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[5] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .2. 1-CHROMA-1,3-BUTADIENES AND 1-CHROMA-1,3,5-HEXATRIENES FROM (CO)5CR=C(OC2H5)CH3 BY CARBONYL OLEFINATION CATALYZED WITH TRIETHYLAMINE CHLOROTRIMETHYLSILANE [J].

AUMANN, R ;

HEINEN, H .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (04) :537-540

[6] Physical organic chemistry of transition metal carbene complexes.: 12.: Spectroscopic detection and kinetic characterization of the intermediate in the nucleophilic substitution reaction of (CO)5Cr=C(OCH3)Ph with thiolate ions in aqueous acetonitrile [J].

Bernasconi, CF ;

Flores, FX ;

Kittredge, KW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (31) :7983-7984

[7] PHYSICAL ORGANIC-CHEMISTRY OF TRANSITION-METAL CARBENE COMPLEXES .2. KINETICS AND MECHANISM OF REACTIONS OF [METHOXY(PHENYL)CARBENE]PENTACARBONYLCHROMIUM(0) WITH PRIMARY ALIPHATIC-AMINES IN AQUEOUS ACETONITRILE [J].

BERNASCONI, CF ;

STRONACH, MW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1341-1346

[8] EFFICIENT ENTRY TO BICYCLIC LACTONES VIA VANHALBAN-WHITE CYCLIZATIONS [J].

BRANDVOLD, TA ;

WULFF, WD ;

RHEINGOLD, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (04) :1645-1647

[9] Palladium-catalysed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines [J].

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Moro, L ;

Pace, P .

TETRAHEDRON, 1996, 52 (30) :10225-10240

[10] GENERATION AND REACTIONS OF (PHENYLMETHYLCARBENE)PENTACARBONYLTUNGSTEN(O) [J].

CASEY, CP ;

ALBIN, LD ;

BURKHARDT, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) :2533-2539

← 1 2 3 4 5 6 7 →