Recent Advances in Catalytic Stereocontrolled Cycloaddition with Terminal Propargylic Compounds

被引：70

作者：

Hu, Xin-Hu ^{[1
]}

Liu, Zhen-Ting ^{[1
]}

Shao, Long ^{[1
]}

Hu, Xiang-Ping ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 07期

关键词：

cycloaddition; asymmetric catalysis; propargylic compound; ruthenium; copper; palladium; gold; SESQUITERPENE HYDROQUINONE DERIVATIVES; FUNCTIONALLY-SUBSTITUTED ARYL; ENANTIOSELECTIVE SYNTHESIS; ALLENYLIDENE COMPLEXES; CARBON NUCLEOPHILES; BETA-KETOESTERS; AMINATION; ACETATES; CONSTRUCTION; ESTERS;

D O I：

10.1055/s-0034-1379968

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Terminal propargylic compounds containing an alkyne unit and an alcohol or ester group in the propargylic position have a fairly acidic acetylenic hydrogen atom; this makes them versatile substrates for further chemical transformation. Some transition metals such as ruthenium or copper exhibit specific affinity for terminal propargylic compounds, generating dielectrophilic ruthenium- or copper-allenylidene complexes that show high potential for stereoselective cycloaddition with various bis-nucleophiles. In this review, we highlight this emerging field of catalytic stereoselective cycloaddition with terminal propargylic compounds. Examples of ruthenium-, copper-, palladium-, and gold-catalyzed cycloaddition are given in the article, along with mechanistic considerations. 1 Introduction 2 Ruthenium-Allenylidene Complexes in Enantioselective Cycloaddition 3 Copper-Allenylidene Complexes in Enantioselective Cycloaddition 4 Palladium-Propargyl Complexes in Stereoselective Cycloaddition 5 Gold-Carbenoid Complexes in Stereoselective Cycloaddition 6 Summary and Outlook

引用

页码：913 / 923

页数：11

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