Scope of the intramolecular titanocene-catalyzed Pauson-Khand type reaction

被引：113

作者：

Hicks, FA ^{[1
]}

Kablaoui, NM ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 25期

关键词：

D O I：

10.1021/ja990682u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Pauson-Khand type conversion of enynes to bicyclic cyclopentenones employing the commercially available precatalyst titanocene dicarbonyl is described. This methodology shows excellent functional group tolerance for a group 4 metallocene-catalyzed process. The scope and limitations of this cyclization with respect to 1,6-, 1,7- and 1,8-enynes with a variety of terminal alkyne substituents, chiral enynes, and enynes containing substituted olefins are described in detail. A mechanism involving carbonylation of an intermediate titanacyclopentene has been proposed.

引用

收藏

页码：5881 / 5898

页数：18

相关论文

共 112 条

[1] HIGHLY STEREOCONTROLLED AND REGIOCONTROLLED CYCLOPENTANNULATION VIA ALLYLPHOSPHONATE CONJUGATE ADDITION AND HYDROBORATION OXIDATION ELIMINATION - SYNTHESIS OF PENTALENIC ACID WITH VIRTUALLY COMPLETE STEREOCONTROL AND REGIOCONTROL [J].

AGNEL, G ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7424-7426

[2] DIASTEREOSELECTIVE ZIRCONOCENE-PROMOTED BICYCLIZATION-CARBONYLATION OF ALLYLICALLY METHYL-SUBSTITUTED ENYNES - SYNTHESIS OF (+)-IRIDOMYRMECIN [J].

AGNEL, G ;

OWCZARCZYK, Z ;

NEGISHI, E .

TETRAHEDRON LETTERS, 1992, 33 (12) :1543-1546

[3] Pauson-Khand cycloaddition of alpha,omega-allenynes. [J].

Ahmar, M ;

Locatelli, C ;

Colombier, D ;

Cazes, B .

TETRAHEDRON LETTERS, 1997, 38 (30) :5281-5284

[4] Zirconium-mediated intramolecular coupling of terminal alkynes and their subsequent carbonylation: Novel synthesis of seven- and eight-membered heterocycles [J].

Barluenga, J ;

Sanz, R ;

Fananas, FJ .

CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1324-1336

[5] ZIRCONIUM-PROMOTED INTRAMOLECULAR CYCLIZATION OF TERMINAL ALKYNES AND UNUSUAL CARBONYLATION REACTION [J].

BARLUENGA, J ;

SANZ, R ;

FANANAS, FJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (10) :1009-1010

[6] Thermal promotion of the cobalt catalyzed intramolecular Pauson-Khand reaction - An alternative experimental protocol for cyclopentenone synthesis [J].

Belanger, DB ;

O'Mahony, DJR ;

Livinghouse, T .

TETRAHEDRON LETTERS, 1998, 39 (42) :7637-7640

[7] Hexacarbonyldicobalt-alkyne complexes as convenient Co2(CO)8 surrogates in the catalytic Pauson-Khand reaction [J].

Belanger, DB ;

Livinghouse, T .

TETRAHEDRON LETTERS, 1998, 39 (42) :7641-7644

[8] DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION [J].

BERK, SC ;

GROSSMAN, RB ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8593-8601

[9] TITANOCENE-CATALYZED CONVERSION OF ENYNES TO BICYCLIC CYCLOPENTENONES [J].

BERK, SC ;

GROSSMAN, RB ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4912-4913

[10] A SIMPLE ORGANOCOBALT MEDIATED SYNTHESIS OF SUBSTITUTED 3-OXABICYCLO[3.3.0]OCT-6-EN-7-ONES [J].

BILLINGTON, DC ;

WILLISON, D .

TETRAHEDRON LETTERS, 1984, 25 (36) :4041-4044

← 1 2 3 4 5 6 7 8 9 10 →