DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION

被引：102

作者：

BERK, SC ^{[1
]}

GROSSMAN, RB ^{[1
]}

BUCHWALD, SL ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 19期

关键词：

D O I：

10.1021/ja00098a020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol % of Cp(2)Ti(PMe(3))(2) in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.

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页码：8593 / 8601

页数：9

相关论文

共 62 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] BASE-CATALYZED INTRAMOLECULAR CYCLOADDITIONS OF ALLYL 3-PHENYLPROP-2-YNYL ETHERS AND 4-METHYLPENT-4-EN-2-YNYL PROP-2-YNYL ETHERS [J].

BARTLETT, AJ ;

LAIRD, T ;

OLLIS, WD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (14) :1315-1320

[4]

BECU C, 1987, B SOC CHIM BELG, V96, P115

[5] 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

[6] (1-ALKENE)(TRIMETHYLPHOSPHINE)ZIRCONOCENES - PREPARATION, CHARACTERIZATION, AND REACTIVITY [J].

BINGER, P ;

MULLER, P ;

BENN, R ;

RUFINSKA, A ;

GABOR, B ;

KRUGER, C ;

BETZ, P .

CHEMISCHE BERICHTE, 1989, 122 (06) :1035-1042

[7] ZIRCONOCENE COMPLEXES OF UNSATURATED ORGANIC-MOLECULES - NEW VEHICLES FOR ORGANIC-SYNTHESIS [J].

BROENE, RD ;

BUCHWALD, SL .

SCIENCE, 1993, 261 (5129) :1696-1701

[8] GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].

BUCHWALD, SL ;

NIELSEN, RB .

CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058

[9] SYNTHESIS AND X-RAY CRYSTAL-STRUCTURE OF THE ZIRCONOCENE COMPLEX OF A CYCLOPENTYNE AND ITS USE TO PREPARE BICYCLIC CYCLOPENTENONES [J].

BUCHWALD, SL ;

LUM, RT ;

FISHER, RA ;

DAVIS, WM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) :9113-9114

[10] ASYMMETRIC APPROACH TO PAUSON-KHAND BICYCLIZATION - ENANTIOSELECTIVE FORMAL SYNTHESIS OF HIRSUTENE [J].

CASTRO, J ;

SORENSEN, H ;

RIERA, A ;

MORIN, C ;

MOYANO, A ;

PERICAS, MA ;

GREENE, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9388-9389

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