PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems

被引：208

作者：

Harrak, Y ^{[1
]}

Blaszykowski, C ^{[1
]}

Bernard, M ^{[1
]}

Cariou, K ^{[1
]}

Mainetti, E ^{[1
]}

Mouriès, V ^{[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：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 28期

关键词：

D O I：

10.1021/ja0474695

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

5-En-1-yn-3-ol substrates bearing a free hydroxyl group or an acyl group are highly versatile partners for PtCl2-catalyzed cycloisomerizations. Electrophilic activation of the alkyne moiety triggers at wish a hydride or an O-acyl migration yielding at the end to regioisomeric keto derivatives. The efficient preparation of Sabina ketone, an important monoterpene precursor, has been worked out. Copyright © 2004 American Chemical Society.

引用

页码：8656 / 8657

页数：2

共 22 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] Enantioselective synthesis of sabina ketone
Barberis, M
Pérez-Prieto, J
[J]. TETRAHEDRON LETTERS, 2003, 44 (35) : 6683 - 6685
[3] 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
[4] CHAMAULT L, 2004, CHEM COMMUN, P850
[5] 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
[6] Platinum-catalyzed cycloisomerization reactions of enynes
Fürstner, A
Stelzer, F
Szillat, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 11863 - 11869
[7] 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
[8] A short and efficient synthesis of (±)-trans-sabinene hydrate
Galopin, CC
[J]. TETRAHEDRON LETTERS, 2001, 42 (33) : 5589 - 5591
[9] Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones
Kirschberg, T
Mattay, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8885 - 8896
[10] Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions
Lloyd-Jones, GC
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) : 215 - 236

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