Stereoselective synthesis of silyl enol ethers via the iridium-catalyzed isomerization of allyl silyl ethers

被引：63

作者：

Ohmura, T ^{[1
]}

Yamamoto, Y ^{[1
]}

Miyaura, N ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 0608628, Japan

来源：

ORGANOMETALLICS | 1999年 / 18卷 / 03期

关键词：

D O I：

10.1021/om980794e

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective isomerization of allyl silyl ethers to (E)- or (Z)-silyl enol ethers was carried out in the presence of a cationic iridium(I) catalyst. The complex, prepared in situ by treating [Ir(cod)(2)]PF6/2PPr(3) with hydrogen, was found to be an excellent catalyst for the isomerization of primary and secondary allyl ethers in high yields. The primary allyl silyl ethers produced (E)-enol ethers and the secondary allyl ethers afforded (Z)-enol ethers with high stereoselectivity, often exceeding 99%.

引用

页码：413 / 416

页数：4

共 61 条

[1] STRUCTURE OF AN IRIDIUM-CONTAINING HYDROGENATION CATALYST [J].

ABBASSIOUN, MS ;

HITCHCOCK, PB ;

CHALONER, PA .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :331-333

[2] ISOMERIZATION OF ALLYL ETHERS CATALYZED BY CATIONIC IRIDIUM COMPLEX [IR(CYCLO-OCTA-1,5-DIENE)(PMEPH2)2]PF6 - HIGHLY STEREOSELECTIVE ROUTE TO TRANS-PROPENYL ETHERS [J].

BAUDRY, D ;

EPHRITIKHINE, M ;

FELKIN, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :694-695

[3]

BOECKEL CAA, 1979, TETRAHEDRON LETT, P3561

[4] PRODUCTS FORMED FROM RHODIUM TRICHLORIDE TRIHYDRATE AND ALLYL ALCOHOL OR DIALLYL ETHER - CRYSTAL AND MOLECULAR STRUCTURE OF [RH2CL4(C6H11O)2], CH3OH [J].

BRIGHT, A ;

NICHOLSON, JK ;

POWELL, J ;

SHAW, BL ;

MALONE, JF .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (13) :712-+

[5] NATURE OF THE CATALYTIC CYCLE IN IRIDIUM-COMPLEX CATALYZED HYDROGENATION OF UNSATURATED ALCOHOLS [J].

BROWN, JM ;

DEROME, AE ;

HALL, SA .

TETRAHEDRON, 1985, 41 (20) :4647-4656

[6] COMPARISON OF CATIONIC RHODIUM AND IRIDIUM COMPLEXES IN DIRECTED HOMOGENEOUS HYDROGENATION [J].

BROWN, JM ;

HALL, SA .

TETRAHEDRON, 1985, 41 (20) :4639-4646

[7]

BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P85

[8]

BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P1

[9] HOMOGENEOUS HYDROGENATION OF TETRASUBSTITUTED ALKENE MOIETIES IN PROCHIRAL DIDEHYDRO AMINO-ACID DERIVATIVES CATALYZED BY IRIDIUM COMPLEXES [J].

CABEZA, JA ;

CATIVIELA, C ;

DEVILLEGAS, MDD ;

ORO, LA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1881-1884

[10] ISOMERIZATION OF ALLYL ETHERS TO VINYL ETHERS CATALYZED BY PALLADIUM ON CARBON [J].

CARLESS, HAJ ;

HAYWOOD, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (20) :980-981

← 1 2 3 4 5 6 7 →