Gold-Catalyzed One-Step Construction of 2,3-Dihydro-1H-Pyrrolizines with an Electron-Withdrawing group in the 5-position: A Formal Synthesis of 7-Methoxymitosene

被引：136

作者：

Yan, Ze-Yi ^{[1
]}

Xiao, Yuanjing ^{[1
]}

Zhang, Liming ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 34期

基金：

美国国家科学基金会;

关键词：

carbene; gold; homogeneous catalysis; mitosene; nitrene; CYCLOISOMERIZATION; DERIVATIVES; PYRROLE; COMPLEXES; EFFICIENT; PLATINUM; ACCESS;

D O I：

10.1002/anie.201203678

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

What a ring formation! Bicyclic dihydropyrrolizines with an electron-withdrawing group (EWG) at the 5-position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically-controlled regioselectivity, and the generation of destabilized 1-azapentadienium ions and their pericyclic reactions. This method was used for a formal synthesis of 7-methoxymitosene (see scheme).

引用

页码：8624 / 8627

页数：4

共 57 条

[51] Gold-Catalyzed Transformation of 2-Alkynyl Arylazides: Efficient Access to the Valuable Pseudoindoxyl and Indolyl Frameworks [J].

Wetzel, Alexander ;

Gagosz, Fabien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) :7354-7358

[52]

Ye L., 2011, ANGEW CHEM, V123, P3294

[53] A Flexible and Stereoselective Synthesis of Azetidin-3-ones through Gold-Catalyzed Intermolecular Oxidation of Alkynes [J].

Ye, Longwu ;

He, Weimin ;

Zhang, Liming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (14) :3236-3239

[54] Gold-Catalyzed One-Step Practical Synthesis of Oxetan-3-ones from Readily Available Propargylic Alcohols [J].

Ye, Longwu ;

He, Weimin ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (25) :8550-+

[55] Alkynes as Equivalents of α-Diazo Ketones in Generating α-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones [J].

Ye, Longwu ;

Cui, Li ;

Zhang, Guozhu ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3258-+

[56]

Yeom H.-S., 2010, Angew. Chem, V122, P1655

[57] Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6 Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade [J].

Yeom, Hyun-Suk ;

Lee, Youngun ;

Jeong, Jaewon ;

So, Eunsoo ;

Hwang, Soojin ;

Lee, Ji-Eun ;

Lee, Shim Sung ;

Shin, Seunghoon .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) :1611-1614

← 1 2 3 4 5 6 →