Steric hindrance facilitated synthesis of enynes and their intramolecular [4+2] cycloaddition with alkynes

被引：37

作者：

González, JJ ^{[1
]}

Francesch, A ^{[1
]}

Cárdenas, DJ ^{[1
]}

Echavarren, AM ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 09期

关键词：

D O I：

10.1021/jo9717853

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.

引用

页码：2854 / 2857

页数：4

共 44 条

[1] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].

ALAMI, M ;

FERRI, F ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406

[2] THE PALLADIUM-CATALYZED REDUCTIVE ADDITION OF ARYL IODIDES TO PROPARGYL ALCOHOLS - A ROUTE TO GAMMA,GAMMA-DIARYL ALLYLIC ALCOHOLS [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON, 1985, 41 (22) :5121-5131

[3] PERI INTERACTION IN NAPHTHALENE DERIVATIVES [J].

BALASUBRAMANIYAN, V .

CHEMICAL REVIEWS, 1966, 66 (06) :567-+

[4] Silver salts as new catalyst for coupling reactions; Synthesis of epoxyenynes [J].

Bertus, P ;

Pale, P .

TETRAHEDRON LETTERS, 1996, 37 (12) :2019-2022

[5] INTERACTIONS AND CHEMISTRY OF 1,8-BIS(PHENYLETHYNYL)-NAPHTHALENE AND 1,8-BIS(1-ALKYNYL)NAPHTHALENES [J].

BOSSENBROEK, B ;

SANDERS, DC ;

CURRY, HM ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (02) :371-+

[6] TOTAL SYNTHESIS OF IONOPHORE ANTIBIOTIC X-14547A (INDANOMYCIN) [J].

BURKE, SD ;

PISCOPIO, AD ;

KORT, ME ;

MATULENKO, MA ;

PARKER, MH ;

ARMISTEAD, DM ;

SHANKARAN, K .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :332-347

[7] Strained cyclic cumulene intermediates in Diels-Alder cycloadditions of enynes and diynes [J].

Burrell, RC ;

Daoust, KJ ;

Bradley, AZ ;

DiRico, KJ ;

Johnson, RP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4218-4219

[8] CYCLOALLENES .8. 1,2,4-CYCLOHEXATRIENE, AN ISOBENZENE, AND BICYCLO[4.4.0]DECA-1,3,5,7,8-PENTAENE, AN ISONAPHTHALENE - GENERATION AND TRAPPING REACTIONS [J].

CHRISTL, M ;

BRAUN, M ;

MULLER, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (04) :473-476

[9] INTRAMOLECULAR [4+2] CYCLOADDITION REACTIONS OF CONJUGATED ENYNES [J].

DANHEISER, RL ;

GOULD, AE ;

DELAPRADILLA, RF ;

HELGASON, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5514-5515

[10] SYNTHESIS OF A CHIRAL BINAPHTHYLDISULFIDE - A POTENTIALLY USEFUL REAGENT FOR CATALYTIC ASYMMETRIC-SYNTHESIS [J].

FELDMAN, KS ;

RUCKLE, RE ;

ENSEL, SM ;

WEINREB, PH .

TETRAHEDRON LETTERS, 1992, 33 (47) :7101-7102

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