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
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
[91]   N-OXIDE PROMOTED PAUSON-KHAND CYCLIZATIONS AT ROOM-TEMPERATURE [J].
SHAMBAYATI, S ;
CROWE, WE ;
SCHREIBER, SL .
TETRAHEDRON LETTERS, 1990, 31 (37) :5289-5292
[92]  
SMIT WA, 1989, SYNTHESIS-STUTTGART, P472
[93]   A titanocene-catalyzed intramolecular ene reaction: Cycloisomerization of enynes and dienynes [J].
Sturla, SJ ;
Kablaoui, NM ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) :1976-1977
[94]   The Pauson-Khand reaction catalyzed by the methylidynetricobalt nonacarbonyl cluster [J].
Sugihara, T ;
Yamaguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10782-10783
[95]   Rate enhancement of the Pauson-Khand reaction by primary amines [J].
Sugihara, T ;
Yamada, M ;
Ban, H ;
Yamaguchi, M ;
Kaneko, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2801-2804
[96]  
TAKACS BE, 1990, TETRAHEDRON LETT, V31, P2865
[97]   INTRAMOLECULAR FORMAL IRON-CATALYZED ENE REACTIONS - THE STEREOSELECTIVE AND REGIOCONTROLLED FORMATION OF SUBSTITUTED TETRAHYDROPYRANS [J].
TAKACS, JM ;
ANDERSON, LG ;
CRESWELL, MW ;
TAKACS, BE .
TETRAHEDRON LETTERS, 1987, 28 (46) :5627-5630
[98]   INTRAMOLECULAR FORMAL IRON-CATALYZED ENE REACTIONS - NEW AND HIGHLY STEREOSELECTIVE IRON-CATALYZED CARBOCYCLIZATIONS OF TRIENE ETHERS [J].
TAKACS, JM ;
ANDERSON, LG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2200-2202
[99]   CATALYTIC IRON-MEDIATED ENE CARBOCYCLIZATIONS OF TRIENES - ENANTIOSELECTIVE SYNTHESES OF THE IRIDOID MONOTERPENES (-)-MITSUGASHIWALACTONE AND (+)-ISOIRIDOMYRMECIN [J].
TAKACS, JM ;
MYOUNG, YC .
TETRAHEDRON LETTERS, 1992, 33 (03) :317-320
[100]   PALLADIUM-CATALYZED CYCLOISOMERIZATIONS OF ENYNES AND RELATED REACTIONS [J].
TROST, BM .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (02) :34-42