Synthesis of substituted 1,4-dienes by direct alkylation of allylic alcohols

被引：50

作者：

Kolundzic, Filip ^{[1
]}

Micalizio, Glenn C. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 49期

关键词：

D O I：

10.1021/ja075678u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A regio- and stereoselective cross-coupling reaction between unactivated allylic alcohols and alkynes is described for the synthesis of 1,4-dienes.

引用

页码：15112 / +

页数：3

共 18 条

[1] Ruthenium-catalysed coupling of allyl alcohol with alkynes: A new route to gamma delta-unsaturated acetals and aldehydes [J].

Derien, S ;

Jan, D ;

Dixneuf, PH .

TETRAHEDRON, 1996, 52 (15) :5511-5524

[2] ALKYLATION OF ALLYLIC DERIVATIVES - ON THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF ALKYLATION OF ALLYLIC ALCOHOLS BY THE MURAHASHI METHOD [J].

GOERING, HL ;

KANTNER, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (10) :2144-2148

[3] GENERATION AND REACTIONS OF LOW-VALENT TITANIUM ALKOXIDE-ACETYLENE COMPLEXES - A PRACTICAL PREPARATION OF ALLYL ALCOHOLS [J].

HARADA, K ;

URABE, H ;

SATO, F .

TETRAHEDRON LETTERS, 1995, 36 (18) :3203-3206

[4]

Kazmaier U., 2004, METAL CATALYZED CROS, P531

[5] NUCLEOPHILIC AND ORGANOMETALLIC DISPLACEMENT-REACTIONS OF ALLYLIC COMPOUNDS - STEREOCHEMISTRY AND REGIOCHEMISTRY [J].

MAGID, RM .

TETRAHEDRON, 1980, 36 (13) :1901-1930

[6] An alkoxide-directed intermolecular [2+2+1] annulation:: A three-component coupling reaction for the synthesis of tetrasubstituted α,β,-unsaturated γ-lactams [J].

McLaughlin, Martin ;

Takahashi, Masayuki ;

Micalizio, Glenn C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3912-3914

[7] A site- and stereoselective intermolecular alkene-alkyne coupling process [J].

Reichard, Holly A. ;

Micalizio, Glenn C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1440-1443

[8] An alkoxide-directed carbometalation of internal alkynes [J].

Ryan, J ;

Micalizio, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2764-2765

[9]

Sato F, 2002, TITANIUM AND ZIRCONIUM IN ORGANIC SYNTHESIS, P319, DOI 10.1002/3527600671.ch9

[10] Regio- and stereoselective cross-coupling of substituted olefins and imines. A convergent stereoselective synthesis of saturated 1,5-aminoalcohols and substituted piperidines [J].

Takahashi, Masayuki ;

Micalizio, Glenn C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7514-+

← 1 2 →