From Straightforward Gold(I)-Catalyzed Enyne Cyclizations to more Demanding Intermolecular Reactions of Alkynes with Alkenes

Abstract

Gold(I) complexes are the catalysts of choice for the selective activation of alkynes in the presence of other unsaturated functional groups. In this Account, we present the development of gold(I)-catalyzed intermolecular reactions of terminal alkynes with functionalized alkenes. In particular, we focus on the synthesis of cyclobutenes by asymmetric gold(I)-catalyzed [2+2] cycloaddition and its applications.

1 Introduction

2 Intramolecular Gold(I)-Catalyzed Synthesis of Cyclobutenes

2.1 Role of Cyclobutenes in 1,n-Enynes Cycloisomerizations

2.2 [2+2] Cycloaddition of 1,n-Enynes

3 Intermolecular Gold(I)-Catalyzed Reactions of Terminal Alkynes with Alkenes

3.1 [2+2] Cycloaddition of Alkynes with Alkenes

3.2 Reactions of Propiolic Acid with Alkenes

3.3 [2+2+2] Cycloaddition of Alkynes with Oxoalkenes

3.4 Reaction of Alkynes with Furanes

4 Gold(I)-Catalyzed Enantioselective Synthesis of Cyclobutenes

5 Concluding Remarks

Key words

gold - alkynes - alkenes - cycloaddition - cyclobutenes - asymmetric catalysis

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