FACILE FORMATION OF 7-MEMBERED AND 8-MEMBERED CYCLOALKENES VIA CATALYTIC AND CYCLIC CARBOPALLADATION OF ALLENES

被引：69

作者：

MA, SM ^{[1
]}

NEGISHI, E ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 17期

关键词：

D O I：

10.1021/jo00096a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of allene-containing aryl and alkenyl halides under the influence of a catalytic amount of a Pd-phosphine complex, e.g., Cl2Pd(PPh(3))(2), proceeds via carbon-carbon bond formation at the central carbon atom of the allene moiety, providing a novel and facile route to seven- and eight-membered cycloalkene derivatives.

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页码：4730 / 4732

页数：3

相关论文

共 25 条

[1]

ABELMAN MM, 1987, J ORG CHEM, V52, P4133

[2] SYNTHESIS OF 1,3-DIENES AND FUNCTIONALIZED STYRENES BY CATALYTIC CARBOPALLADATION OF ALLENES [J].

AHMAR, M ;

CAZES, B ;

GORE, J .

TETRAHEDRON LETTERS, 1984, 25 (40) :4505-4508

[3] SYNTHETIC METHODOLOGY INVOLVING THE CARBOPALLADATION OF ALLENES [J].

CAZES, B .

PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1867-1878

[4] ENANTIOSELECTIVE SYNTHESIS OF PUMILIOTOXIN-251D - A STRATEGY EMPLOYING AN ALLENE-BASED ELECTROPHILE-MEDIATED CYCLIZATION [J].

FOX, DNA ;

LATHBURY, D ;

MAHON, MF ;

MOLLOY, KC ;

GALLAGHER, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2652-2656

[5] RHODIUM-CATALYZED AND PALLADIUM-CATALYZED FORMATION OF CONJUGATED MONO-EXOCYCLIC AND BIS-EXOCYCLIC DIENES - 5-EXO-TRIG-VERSUS 6-ENDO-TRIG CYCLIZATIONS [J].

GRIGG, R ;

STEVENSON, P ;

WORAKUN, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (16) :1073-1075

[6] PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSELECTIVE ALLYLAMINATION OF ALLENIC ALCOHOLS [J].

KIMURA, M ;

FUGAMI, K ;

TANAKA, S ;

TAMARU, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6377-6379

[7] SYNTHESIS OF BICYCLIC AND POLYCYCLIC ALKENES VIA PALLADIUM-CATALYZED INTRAMOLECULAR ARYLATION AND VINYLATION [J].

LAROCK, RC ;

SONG, H ;

BAKER, BE ;

GONG, WH .

TETRAHEDRON LETTERS, 1988, 29 (24) :2919-2922

[8] REGIOSELECTIVE, PALLADIUM-CATALYZED HETEROANNULATION AND CARBOANNULATION OF 1,2-DIENES USING FUNCTIONALLY SUBSTITUTED ARYL HALIDES [J].

LAROCK, RC ;

BERRIOSPENA, NG ;

FRIED, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2615-2617

[9] A CONCISE SYNTHESIS OF A HIGHLY FUNCTIONALIZED C-ARYL TAXOL ANALOG BY AN INTRAMOLECULAR HECK OLEFINATION REACTION [J].

MASTERS, JJ ;

JUNG, DK ;

BORNMANN, WG ;

DANISHEFSKY, SJ ;

DEGALA, S .

TETRAHEDRON LETTERS, 1993, 34 (45) :7253-7256

[10] PALLADIUM-CATALYZED CYCLIZATIONS OF BROMO DIENES [J].

NARULA, CK ;

MAK, KT ;

HECK, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (17) :2792-2796