Microwave-assisted allylation of acetals with allyltrimethylsilane in the presence of CuBr

被引：28

作者：

Jung, ME ^{[1
]}

Maderna, A ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 22期

关键词：

D O I：

10.1021/jo049015w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the first synthesis of homoallyl ethers from acetals and allyltrimethylsilane using microwave heating and CuBr as a promoter. This method works best for aromatic acetals, giving the corresponding homoallyl ethers in good to quantitative yield.

引用

页码：7755 / 7757

页数：3

共 23 条

[1] INTRAMOLECULAR META PHOTOCYCLOADDITION OF CONFORMATIONALLY RESTRAINED 5-PHENYLPENT-1-ENES .2. STERIC AND ELECTRONIC EFFECTS CAUSED BY 4-MONOSUBSTITUTION AND 4-DISUBSTITUTION [J].

BARENTSEN, HM ;

SIEVAL, AB ;

CORNELISSE, J .

TETRAHEDRON, 1995, 51 (27) :7495-7520

[2] Group 13 trihalide complexes of 9-fluorenone: a comparison of methods for assigning relative Lewis acidity [J].

Branch, CS ;

Bott, SG ;

Barron, AR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 666 (1-2) :23-34

[3] ELECTRONEGATIVITY AND LEWIS ACID STRENGTH [J].

BROWN, ID ;

SKOWRON, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3401-3403

[4] THE LEWIS ACID COMPLEXES OF ALPHA,BETA-UNSATURATED CARBONYL AND NITRILE COMPOUNDS .1. A NUCLEAR MAGNETIC-RESONANCE STUDY [J].

CHILDS, RF ;

MULHOLLAND, DL ;

NIXON, A .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (06) :801-808

[5] A SCALE OF RELATIVE LEWIS ACIDITIES FROM PROTON MAGNETIC RESONANCE DATA [J].

DETERS, JF ;

MCCUSKER, PA ;

PILGER, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (17) :4583-&

[6]

HOLLIS TH, 1993, TETRAHEDRON LETT, V35, P4309

[7] CHEMISTRY OF ORGANOSILICON COMPOUNDS .91. ALLYLSILANES AS SYNTHETIC INTERMEDIATES .2. SYNTHESES OF HOMOALLYL ETHERS FROM ALLYLSILANES AND ACETALS PROMOTED BY TITANIUM TETRACHLORIDE [J].

HOSOMI, A ;

ENDO, M ;

SAKURAI, H .

CHEMISTRY LETTERS, 1976, (09) :941-942

[8] CHEMISTRY OF ORGANOSILICON COMPOUNDS .3. SELECTIVE ALLYLATIONS OF ALPHA,BETA-UNSATURATED ACETALS WITH ALLYLSILANES IN PRESENCE OF LEWIS ACID [J].

HOSOMI, A ;

ENDO, M ;

SAKURAI, H .

CHEMISTRY LETTERS, 1978, (05) :499-502

[9]

ISHIIA, 1997, SYNLETT, P1145

[10] Allylation of acetals and ketals with allyltrimethylsilane catalyzed by the mixed Lewis acid system AlBr3/CuBr [J].

Jung, ME ;

Maderna, A .

TETRAHEDRON LETTERS, 2004, 45 (27) :5301-5304

← 1 2 3 →