A STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED ALKENES .1. NICKEL-CATALYZED COUPLING OF GRIGNARD-REAGENTS WITH 5-ALKYL-2,3-DIHYDROFURANS

被引：28

作者：

KOCIENSKI, PJ

PRITCHARD, M

WADMAN, SN

WHITBY, RJ

YEATES, CL

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 24期

关键词：

D O I：

10.1039/p19920003419

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Alkyl-2,3-dihydrofurans 3a-j prepared by the alkylation of 5-lithio-2,3-dihydrofuran 2 with primary alkyl bromides and iodides, undergo Ni0-catalysed coupling with Grignard reagents to give homoallylic alcohols. The yield and stereoselectivity depend on the structure of the Grignard reagent with the best results being obtained with long chain primary Grignard reagents and Grignard reagents lacking beta-hydrogens (Me, Ph, Me3SiCH2) . 5-(1-Hydroxyalkyl)-2,3-dihydrofurans 20 and 21 are poor substrates for the coupling reaction. Mechanisms are proposed for the coupling as well as competing reduction and isomerisation reactions.

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页码：3419 / 3429

页数：11

相关论文

共 46 条

[1] CYCLIC VINYL ETHER CARBANIONS .2. PREPARATION AND APPLICATIONS TO THE SYNTHESIS OF CARBONYL-COMPOUNDS [J].

BOECKMAN, RK ;

BRUZA, KJ .

TETRAHEDRON, 1981, 37 (23) :3997-4006

[2] SOME COMPLEXES OF DITERTIARY PHOSPHINES WITH NICKEL(2) AND NICKEL(3) [J].

BOOTH, G ;

CHATT, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAY) :3238-&

[3] TOTAL SYNTHESIS OF (+/-)-MULTIFIDENE, THE GAMETE ATTRACTANT OF THE PHAEOPHYTE CUTLERIA-MULTIFIDA [J].

CROUSE, GD ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (21) :4272-4274

[4] KETONE ENOLATES - REGIOSPECIFIC PREPARATION AND SYNTHETIC USES [J].

DANGELO, J .

TETRAHEDRON, 1976, 32 (24) :2979-2990

[5] TRANSITION-METAL-PROMOTED ALKYLATIONS OF UNSATURATED ALCOHOLS - THE SELECTIVE METHYLATION OF HOMOPROPARGYL ALCOHOLS VIA TITANIUM TETRACHLORIDE TRIMETHYLALUMINUM [J].

EWING, JC ;

FERGUSON, GS ;

MOORE, DW ;

SCHULTZ, FW ;

THOMPSON, DW .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) :2124-2128

[6]

FABRE JL, 1985, B SOC CHIM FR, P772

[7] REACTION OF ORGANOMAGNESIUM COMPOUNDS WITH ALLYLIC ALCOHOLS IN PRESENCE OF NICKEL-COMPLEXES .2. HYDROGENOLYSIS OF ALLYLIC ALCOHOLS [J].

FELKIN, H ;

JAMPELCOSTA, E ;

SWIERCZEWSKI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 134 (03) :265-279

[8] ACTIVATION OF GRIGNARD-REAGENTS BY TRANSITION-METAL COMPOUNDS [J].

FELKIN, H ;

SWIERCZEWSKI, G .

TETRAHEDRON, 1975, 31 (22) :2735-2748

[9]

FIANDANESE V, 1987, SYNTHESIS-STUTTGART, P1034

[10] DIELS-ALDER REACTIONS OF CYCLOALKENONES .4. SHORT SYNTHESES OF SOME CADINENES [J].

FRINGUELLI, F ;

PIZZO, F ;

TATICCHI, A ;

FERREIRA, VF ;

MICHELOTTI, EL ;

PORTER, B ;

WENKERT, E .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :890-891

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