Reorganization of enynes catalyzed by platinum salts

被引：67

作者：

Añorbe, L ^{[1
]}

Domínguez, G ^{[1
]}

Pérez-Castells, J ^{[1
]}

机构：

[1] Univ San Pablo, Dept Quim, Fac Ciencias Expt & Salud, CEU, Madrid 28668, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2004年 / 10卷 / 20期

关键词：

alkynes; cyclization; enynes; platinum; synthetic methods;

D O I：

10.1002/chem.200400089

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Activation of alkynes with platinum salts allows their reaction with alkenes, giving rise to a myriad of interesting processes like cyclizations, formation of cyclopropanes, or metathesis. Weak nucleophiles can also participate in the processes leading to alkoxycyclizations. There are intriguing mechanistic aspects of these processes in which subtle variations of the reaction conditions and/or substrate structures can lead to completely different products.

引用

页码：4938 / 4943

页数：6

共 29 条

[1] The behavior of 1,n-enynes in the presence of transition metals
Aubert, C
Buisine, O
Malacria, M
[J]. CHEMICAL REVIEWS, 2002, 102 (03) : 813 - 834
[2] A NOVEL PTCL4-CATALYZED CYCLOREARRANGEMENT OF ALLYL PROPYNYL ETHERS TO 3-OXABICYCLO[4.1.0]HEPTENES
BLUM, J
BEERKRAFT, H
BADRIEH, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) : 5567 - 5569
[3] Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl3
Chatani, N
Inoue, H
Kotsuma, T
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10294 - 10295
[4] 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
Chatani, N
Kataoka, K
Murai, S
Furukawa, N
Seki, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) : 9104 - 9105
[5] PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes
Chatani, N
Furukawa, N
Sakurai, H
Murai, S
[J]. ORGANOMETALLICS, 1996, 15 (03) : 901 - 903
[6] Reaction of allylsilanes and allylstannanes with alkynes catalyzed by electrophilic late transition metal chlorides
Fernández-Rivas, C
Méndez, M
Nieto-Oberhuber, C
Echavarren, AM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) : 5197 - 5201
[7] Metal-catalyzed carbocyclization by intramolecular reaction of allylsilanes and allylstannanes with alkynes
Fernández-Rivas, C
Méndez, M
Echavarren, AM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) : 1221 - 1222
[8] Platinum-catalyzed cycloisomerization reactions of enynes
Fürstner, A
Stelzer, F
Szillat, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 11863 - 11869
[9] Novel rearrangements of enynes catalyzed by PtCl2
Fürstner, A
Szillat, H
Stelzer, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) : 6785 - 6786
[10] Platinum- and acid-catalyzed enyne metathesis reactions:: Mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin
Fürstner, A
Szillat, H
Gabor, B
Mynott, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) : 8305 - 8314

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