Gold-Catalyzed 1,3-Acyloxy Migration/5-exo-dig Cyclization/1,5-Acyl Migration of Diynyl Esters

被引：85

作者：

Leboeuf, David ^{[1
]}

Simonneau, Antoine ^{[1
]}

Aubert, Corinne ^{[1
]}

Malacria, Max ^{[1
]}

Gandon, Vincent ^{[2
]}

Fensterbank, Louis ^{[1
]}

机构：

[1] UPMC Paris 06, IPCM UMR CNRS 7201, F-75252 Paris 05, France

[2] Univ Paris 11, UMR CNRS 8182, F-91405 Orsay, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 30期

关键词：

cycloisomerization; diynes; gold; homogeneous catalysis; CYCLOISOMERIZATION; ACCESS; ACTIVATION; ENYNES;

D O I：

10.1002/anie.201101179

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Working three shifts: Polyconjugated δ-diketones are formed stereoselectively in high yields by the gold-catalyzed rearrangement of 1,6-diyn-3-yl esters. This cascade involves a 1,3-sigmatropic acyloxy shift, a 5-exo-dig cyclization of the resulting allenyne, and an unprecedented 1,5-sigmatropic shift of an acyl fragment. The usefulness of the products was shown by an efficient acid-catalyzed transformation into a complex polycyclic framework. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6868 / 6871

页数：4

共 43 条

[31] An Unusual Access to Medium Sized Cycloalkynes by a New Gold(I)-Catalysed Cycloisomerisation of Diynes [J].

Odabachian, Yann ;

Le Goff, Xavier F. ;

Gagosz, Fabien .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (36) :8966-8970

[32] Gold-catalyzed [2+2] cyclization of alkyne-propargylic pivaloates to fused bicyclic compounds [J].

Oh, Chang Ho ;

Kim, Ahyun .

SYNLETT, 2008, (05) :777-781

[33] Gold-catalyzed cyclizations of alkyne propargylic acetates to 2,3-bis(alkylidene)cycloalkanones and their related benzene derivativest [J].

Oh, Chang Ho ;

Kim, Ahyun .

NEW JOURNAL OF CHEMISTRY, 2007, 31 (10) :1719-1721

[34] Synthetic Studies toward Sordarin: Building Blocks for the Terpenoid Core and for Analogues Thereof [J].

Schule, Arnaud ;

Liang, Huan ;

Vors, Jean-Pierre ;

Ciufolini, Marco A. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) :1587-1597

[35] A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions [J].

Shapiro, Nathan D. ;

Toste, F. Dean .

SYNLETT, 2010, (05) :675-691

[36] SHORT TOTAL SYNTHESES OF (+/-)-SATIVENE AND (+/-)-CIS-SATIVENEDIOL [J].

SIGRIST, R ;

REY, M ;

DREIDING, AS .

HELVETICA CHIMICA ACTA, 1988, 71 (04) :788-807

[37] A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-SATIVENE [J].

SNOWDEN, RL .

TETRAHEDRON LETTERS, 1981, 22 (02) :101-102

[38] Gold-Catalyzed Cyclizations of 1,6-Diynes [J].

Sperger, Christian ;

Fiksdahl, Anne .

ORGANIC LETTERS, 2009, 11 (11) :2449-2452

[39] Gold-Catalyzed Tandem Cyclizations of 1,6-Diynes Triggered by Internal N- and O-Nucleophiles [J].

Sperger, Christian A. ;

Fiksdahl, Anne .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (13) :4542-4553

[40] A highly efficient preparative method of α-ylidene-β-diketones via AuIII-catalyzed acyl migration of propargylic esters [J].

Wang, Shaozhong ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8414-8415

← 1 2 3 4 5 →