Palladium-catalyzed cycloreduction of 5-allen-1-ynes

被引：19

作者：

Oh, CH ^{[1
]}

Jung, SH ^{[1
]}

Park, DI ^{[1
]}

Choi, JH ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 12期

关键词：

allenyne; palladium; cycloreduction; electron-withdrawing group;

D O I：

10.1016/j.tetlet.2004.02.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed cycloreduction of 5-allen-1-ynes gave the corresponding 1,2-bisalkylidenecyclopentanes in excellent chemoselectivity and chemical yields. Incorporating an electron-withdrawing group at the acetylenic position showed to be better substrates for the present cycloreduction. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2499 / 2502

页数：4

相关论文

共 40 条

[1] A rhodium(I)-catalyzed formal allenic Alder ene reaction for the rapid and stereoselective assembly of cross-conjugated trienes [J].

Brummond, KM ;

Chen, HF ;

Sill, P ;

You, LF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15186-15187

[2] Chiral nonracemic α-alkylidene and α-silylidene cyclopentenones from chiral allenes using an intramolecular allenic Pauson-Khand-type cycloaddition [J].

Brummond, KM ;

Kerekes, AD ;

Wan, HH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5156-5163

[3]

Fumie S., 2000, CHEM REV, V100, P2835

[4] ANIONIC APPROACHES TO THE CONSTRUCTION OF CYCLOPENTANOIDS [J].

HUDLICKY, T ;

PRICE, JD .

CHEMICAL REVIEWS, 1989, 89 (07) :1467-1486

[5]

Kang SK, 2002, ANGEW CHEM INT EDIT, V41, P343, DOI 10.1002/1521-3773(20020118)41:2<343::AID-ANIE343>3.0.CO

[6]

2-1

[7] Transition metal-mediated cycloaddition reactions [J].

Lautens, M ;

Klute, W ;

Tam, W .

CHEMICAL REVIEWS, 1996, 96 (01) :49-92

[8] Carbon-carbon bond formation in regio- and stereoselective palladium-catalyzed cyclization of allene-substituted conjugated dienes [J].

Löfstedt, J ;

Franzén, J ;

Bäckvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8015-8025

[9] Pd0-catalyzed three-component tandem double-addition-cyclization reaction:: Stereoselective synthesis of cis-pyrrolidine derivatives [J].

Ma, SM ;

Jiao, N .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4737-4740

[10]

Ma SM, 2002, ANGEW CHEM INT EDIT, V41, P1775, DOI 10.1002/1521-3773(20020517)41:10<1775::AID-ANIE1775>3.0.CO

← 1 2 3 4 →