Ligand-controlled highly stereoselective syntheses of E- and Z-allylsilanes from dienes and aldehydes using nickel complex

被引：65

作者：

Sawaki, R ^{[1
]}

Sato, Y ^{[1
]}

Mori, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 07期

关键词：

D O I：

10.1021/ol049908a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic methods of highly stereocontrolled E- and Z-allylsilanes were developed. When a toluene solution of diene having a silicon moiety and aldehyde was refluxed in the presence of silane using a catalytic amount of Ni(cod)(2) bearing PPh3, E-allylsilane was obtained in high yield. On the other hand, when the reaction was carried out in THF upon heating in the presence of Ni(cod)2, imidazolium salt, Cs2CO3, and PPh3, Z-allylsilane was formed as a sole product.

引用

页码：1131 / 1133

页数：3

共 18 条

[1] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[2] SELECTIVE, ZIRCONIUM-MEDIATED CROSS-COUPLING OF ALKYNES - SYNTHESIS OF ISOMERICALLY PURE 1,3-DIENES AND 1,4-DIIODO 1,3-DIENES [J].

BUCHWALD, SL ;

NIELSEN, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2870-2874

[3]

Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO

[4]

2-Y

[5]

Herrmann WA, 2001, ADV ORGANOMET CHEM, V48, P1

[6] Synthesis, structure and catalytic application of palladium(II) complexes bearing N-heterocyclic carbenes and phosphines [J].

Herrmann, WA ;

Böhm, VPW ;

Gstöttmayr, CWK ;

Grosche, M ;

Reisinger, CP ;

Weskamp, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :616-628

[7]

Jafarpour L, 2001, ADV ORGANOMET CHEM, V46, P181

[8] Novel and highly regio- and stereoselective nickel-catalyzed homoallylation of benzaldehyde with 1,3-dienes [J].

Kimura, M ;

Ezoe, A ;

Shibata, K ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4033-4034

[9] Unexpected results of enyne metathesis using a ruthenium complex containing an N-heterocyclic carbene ligand [J].

Kitamura, T ;

Sato, Y ;

Mori, M .

CHEMICAL COMMUNICATIONS, 2001, (14) :1258-1259

[10] Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate [J].

Sato, Y ;

Sawaki, R ;

Saito, N ;

Mori, M .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :656-662

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