PtCl2-catalyzed transannular cycloisomerization of 1,5-enynes:: A new efficient regio- and stereocontrolled access to tricyclic derivatives

被引：67

作者：

Blaszykowski, C ^{[1
]}

Harrak, Y ^{[1
]}

Gonçalves, MH ^{[1
]}

Cloarec, JM ^{[1
]}

Dhimane, AL ^{[1
]}

Fensterbank, L ^{[1
]}

Malacria, M ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 21期

关键词：

D O I：

10.1021/ol048463n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(GRAPHICS) Transannular PtCL2-catalyzed cycloisomerizations open a new route to cyclopropanic tricyclic systems. Ketones A or C were efficiently prepared from the same cycloundec-5-en-1-yne precursor B, depending on the substituent at the propargylic position (either benzoate or methoxy).

引用

页码：3771 / 3774

页数：4

共 42 条

[1] Aïssa C, 2000, SYNLETT, P1585
[2] 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
[3] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
BLANCHETTE, MA
CHOY, W
DAVIS, JT
ESSENFELD, AP
MASAMUNE, S
ROUSH, WR
SAKAI, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
[4] PtCl2-catalyzed cycloisomerizations of allenynes
Cadran, N
Cariou, K
Hervé, G
Aubert, C
Fensterbank, L
Malacria, M
Marco-Contelles, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3408 - 3409
[5] Comparative effects of conjugated and deconjugated isomeric enones on the transannular Diels-Alder reaction
Caussanel, F
Deslongchamps, P
Dory, YL
[J]. ORGANIC LETTERS, 2003, 5 (25) : 4799 - 4802
[6] Functionalized carbo- and heterocycles via Pt-catalyzed asymmetric alkoxycyclization of 1,6-enynes
Charruault, L
Michelet, V
Taras, R
Gladiali, S
Genêt, JP
[J]. CHEMICAL COMMUNICATIONS, 2004, (07) : 850 - 851
[7] 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
[8] Dhimane A.L., 2001, RADICALS ORGANIC SYN, V2, P350
[9] Dhimane AL, 2002, ANGEW CHEM INT EDIT, V41, P3284, DOI 10.1002/1521-3773(20020902)41:17<3284::AID-ANIE3284>3.0.CO
[10] 2-Z

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