Iron-catalyzed alkenylation of Grignard reagents by enol phosphates

被引：60

作者：

Cahiez, Gerard ^{[1
]}

Gager, Olivier ^{[1
]}

Habiak, Vanessa ^{[1
]}

机构：

[1] CNRS UCP ESCOM, UMR 8123, Lab Synth Organ Select & Chim Organomet, F-95031 Neuville Sur Oise, Cergy Pontoise, France

来源：

SYNTHESIS-STUTTGART | 2008年 / 16期

关键词：

cross-coupling; Grignard reactions; iron; alkenes; stereoselectivity;

D O I：

10.1055/s-2008-1067194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective preparation of trisubstituted olefins can be easily performed from an Z/E-mixture of enol phosphates by reacting only the E-isomer with a Grignard reagent in the presence of Fe(acac)(3). This procedure combines a kinetic differentiation and a stereoselective reaction. The coupling is very chemoselective in the presence of an alkyl chloride, an ester, a ketone or a nitrile.

引用

页码：2636 / 2644

页数：9

共 81 条

[1] α-Sulfinyl carbanions as a new source of olefins [J].

Abramovitch, A ;

Varghese, JP ;

Marek, I .

ORGANIC LETTERS, 2004, 6 (04) :621-623

[2] Iron-catalyzed nucleophilic substitution of allylic acetate [J].

Akermark, Bjorn ;

Sjogren, Magnus P. T. .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2641-2646

[3] 3,5-bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination [J].

Alonso, DA ;

Fuensanta, M ;

Nájera, C ;

Varea, M .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6404-6416

[4] THE REACTION OF ORGANOBORANES WITH LITHIUM-SALTS OF TRISYLHYDRAZONES OF CYCLOALKANONES FOLLOWED BY TREATMENT WITH IODINE [J].

BABA, T ;

AVASTHI, K ;

SUZUKI, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (05) :1571-1572

[5] DIRECT ONE-POT SYNTHESIS OF TERMINAL OLEFINS AND DEUTERIO OLEFINS FROM CARBOXYLIC-ACID CHLORIDES [J].

BARLUENGA, J ;

YUS, M ;

CONCELLON, JM ;

BERNAD, P .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) :3116-3118

[6] Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary 2 alkyl halides with aryl Grignard reagents [J].

Bedford, RB ;

Betham, M ;

Bruce, DW ;

Danopoulos, AA ;

Frost, RM ;

Hird, M .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) :1104-1110

[7] Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].

Bedford, RB ;

Bruce, DW ;

Frost, RM ;

Goodby, JW ;

Hird, M .

CHEMICAL COMMUNICATIONS, 2004, (24) :2822-2823

[8] Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].

Bedford, RB ;

Bruce, DW ;

Frost, RM ;

Hird, M .

CHEMICAL COMMUNICATIONS, 2005, (33) :4161-4163

[9]

BLASZCZAK L, 1976, TETRAHEDRON LETT, P4405

[10] Cobalt-catalyzed dimerization of α-olefins to give linear α-olefin products [J].

Broene, RD ;

Brookhart, M ;

Lamanna, WM ;

Volpe, AF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17194-17195

← 1 2 3 4 5 6 7 8 9 →