Palladium-catalyzed carbocyclization of 1,6-enynes leading to six-membered rings or oxidized five-membered trifluoroacetates

被引：33

作者：

Mikami, K ^{[1
]}

Hatano, M ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2004年 / 101卷 / 16期

关键词：

D O I：

10.1073/pnas.0307217101

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

We describe palladium-catalyzed carbocyclization of 1,6-enynes leading to six-membered rings by water-originated hydride addition. Mechanistic features of this anomalous carbocyclization and isolation of a chiral five-membered C-Pd intermediate as an oxidized form of trifluoroacetate are also reported.

引用

页码：5767 / 5769

页数：3

共 58 条

[1]

Ackermann L, 2001, SYNLETT, P397

[2] Catalytic enantioselective ring-closing metathesis by a chiral biphen-Mo complex [J].

Alexander, JB ;

La, DS ;

Cefalo, DR ;

Hoveyda, AH ;

Schrock, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4041-4042

[3]

Amatore C, 1996, NEW J CHEM, V20, P1143

[4] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[5] A NOVEL PTCL4-CATALYZED CYCLOREARRANGEMENT OF ALLYL PROPYNYL ETHERS TO 3-OXABICYCLO[4.1.0]HEPTENES [J].

BLUM, J ;

BEERKRAFT, H ;

BADRIEH, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5567-5569

[6] PALLADIUM CATALYZED [2+2+2]-CYCLOADDITION REACTIONS VIA CARBOPALLADATION OF 1,6-ENYNES [J].

BROWN, S ;

CLARKSON, S ;

GRIGG, R ;

SRIDHARAN, V .

TETRAHEDRON LETTERS, 1993, 34 (01) :157-160

[7] Rh-catalyzed enyne cycloisomerization [J].

Cao, P ;

Wang, B ;

Zhang, XM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) :6490-6491

[8] Ru(II)- and Pt(II)-catalyzed cycloisomerization of ω-aryl-1-alkynes.: Generation of carbocationic species from alkynes and transition metal halides and its interception by an aromatic ring [J].

Chatani, N ;

Inoue, H ;

Ikeda, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4913-4918

[9] Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of ene-ene-ynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes [J].

Chatani, N ;

Kataoka, K ;

Murai, S ;

Furukawa, N ;

Seki, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9104-9105

[10] PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes [J].

Chatani, N ;

Furukawa, N ;

Sakurai, H ;

Murai, S .

ORGANOMETALLICS, 1996, 15 (03) :901-903

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