Platinum-Catalyzed Tandem Cycloisomerization Reaction of Benzoendiynyl Esters: Regioselective Long-Range 1,5-Acyl Migration

被引：22

作者：

Chen, Zhiyuan ^{[1
]}

Jia, Xuegong

Huang, Jiapian

Yuan, Jianjun

机构：

[1] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 21期

基金：

中国国家自然科学基金;

关键词：

CARBON-MONOXIDE; GOLD; CYCLIZATION; ACTIVATION; PALLADIUM; 1,6-ENYNES; EFFICIENT; ACCESS; REARRANGEMENT; CYCLOADDITION;

D O I：

10.1021/jo5020245

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pt-II-catalyzed intramolecular chemo- and regioselective pentannulation/long-range 1,5-acyl migration reaction is described. This cascade cycloisomerization protocol produces a wide variety of benzofulvene diketones in good to excellent yields with exclusively the Z configuration of the exocyclic double bond of the final product. The O-18 isotope experiment together with C-13 NMR, HRMS, and HMBC analyses confirmed an interesting long-range acyl rearrangement process in this transformation.

引用

页码：10674 / 10681

页数：8

共 63 条

[21] PtCl2-catalyzed rearrangement of methylenecyclopropanes [J].

Furstner, Alois ;

Aissa, Christophe .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6306-6307

[22] Ligand Effect in Platinum-Catalyzed Cycloisomerization of 1,6-Enynes: Water or Carbon Monoxide, a Similar Role despite Distinct Electronic Properties? [J].

Gimbert, Yves ;

Fensterbank, Louis ;

Gandon, Vincent ;

Goddard, Jean-Philippe ;

Lesage, Denis .

ORGANOMETALLICS, 2013, 32 (02) :374-376

[23] Gold(I)-catalysed cycloisomerisation of 1,6-enynes into functionalised allenes [J].

Harrak, Youssef ;

Simonneau, Antoine ;

Malacria, Max ;

Gandon, Vincent ;

Fensterbank, Louis .

CHEMICAL COMMUNICATIONS, 2010, 46 (06) :865-867

[24] Gold-Catalyzed Formal 1,6-Acyloxy Migration Leading to 3,4-Disubstituted Pyrrolidin-2-ones [J].

Hashmi, A. Stephen K. ;

Yang, Weibo ;

Yu, Yang ;

Hansmann, Max M. ;

Rudolph, Matthias ;

Rominger, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (04) :1329-1332

[25] Simple Gold-Catalyzed Synthesis of Benzofulvenesugem-Diaurated Species as "Instant Dual-Activation" Precatalysts [J].

Hashmi, A. Stephen K. ;

Braun, Ingo ;

Noesel, Pascal ;

Schaedlich, Johannes ;

Wieteck, Marcel ;

Rudolph, Matthias ;

Rominger, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (18) :4456-4460

[26] Stereocontrolled Synthesis of Complicated Oxacyclic Compounds via Platinum-Catalyzed [4+2]-Cycloadditions and Annulations of Enynals with Allylic Alcohols [J].

Hsu, Yu-Chia ;

Ting, Chun-Ming ;

Liu, Rai-Shung .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (06) :2090-+

[27] 5-Exo-dig radical cyclization of enediynes: The first synthesis of tin-substituted benzofulvenes [J].

Kovalenko, SV ;

Peabody, S ;

Manoharan, M ;

Clark, RJ ;

Alabugin, IV .

ORGANIC LETTERS, 2004, 6 (14) :2457-2460

[28] Pt(II)- or Au(III)-catalyzed [3+2] cycloaddition of metal-containing azomethine ylides: Highly efficient synthesis of the mitosene skeleton [J].

Kusama, H ;

Miyashita, Y ;

Takaya, J ;

Iwasawa, N .

ORGANIC LETTERS, 2006, 8 (02) :289-292

[29] Gold-Catalyzed 1,3-Acyloxy Migration/5-exo-dig Cyclization/1,5-Acyl Migration of Diynyl Esters [J].

Leboeuf, David ;

Simonneau, Antoine ;

Aubert, Corinne ;

Malacria, Max ;

Gandon, Vincent ;

Fensterbank, Louis .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (30) :6868-6871

[30] Platinum-catalyzed formation of cyclic-ketone-fused indoles from N-(2-alkynylphenyl)lactams [J].

Li, Guotao ;

Huang, Xiaogen ;

Zhang, Liming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (02) :346-349

← 1 2 3 4 5 6 7 →