Rh(I)-catalyzed allenic Pauson-Khand reaction: first construction of the bicyclo[6.3.0]undecadienone ring system

被引：58

作者：

Mukai, C ^{[1
]}

Hirose, T ^{[1
]}

Teramoto, S ^{[1
]}

Kitagaki, S ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan

来源：

TETRAHEDRON | 2005年 / 61卷 / 46期

关键词：

Pauson-Khand reaction; allenyne; bicyclo[6.3.0]undecadienone; 2,3]-sigmatropic rearrangement; RhCl(CO)(2)](2); RhCl(CO)dppp](2);

D O I：

10.1016/j.tet.2005.08.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh(I)-catalyzed Pauson-Khand reaction of allenynes afforded the bicyclo[6.3.0]undecadienones as well as their benzo and furo derivatives. In addition, a novel [RhCl(CO)(2)](2)-catalyzed [2,3]-sigmatropic rearrangement of the sulfinic ester species of propargyl alcohols was developed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：10983 / 10994

页数：12

共 42 条

[31]

PAUSON PL, 1988, ASPECTS MODERN INTER

[32] Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles [J].

Pérez, I ;

Sestelo, JP ;

Sarandeses, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4155-4160

[33] Seven membered rings via intramolecular Pauson-Khand reactions [J].

Pérez-Serrano, L ;

Casarrubios, L ;

Domínguez, G ;

Pérez-Castells, J .

CHEMICAL COMMUNICATIONS, 2001, (24) :2602-2603

[34] Functionalized allenes, haloallenes, and bisallenes via [2,3]/[3,3]-sigmatropic rearrangements and their reactivity [J].

Saalfrank, RW ;

Welch, A ;

Haubner, M ;

Bauer, U .

LIEBIGS ANNALEN, 1996, (02) :171-181

[35]

Schore N. E., 1995, COMPREHENSIVE ORGANO, V12, P703

[36]

Schore N. E., 1991, ORG REACTIONS, V40, P1

[37] TRANSITION-METAL-MEDIATED CYCLO-ADDITION REACTIONS OF ALKYNES IN ORGANIC-SYNTHESIS [J].

SCHORE, NE .

CHEMICAL REVIEWS, 1988, 88 (07) :1081-1119

[38]

SCHORE NE, 1991, COMPREHENSIVE ORGANI, V5, P1037

[39] INTRAMOLECULAR AND INTERMOLECULAR ALLENE-ALKYNE COUPLING REACTIONS BY THE USE OF FE(CO)(4)(NME(3)) [J].

SHIBATA, T ;

KOGA, Y ;

NARASAKA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (03) :911-919

[40]

STIRLING CJM, 1996, CHEM COMMUN, P131

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