Recent Advances in the Synthesis and Reactivity of Vinylcyclopropanes

Abstract

In this review, we present the recent advances in the synthesis and reactivity of vinylcyclopropanes (VCPs). Various important methodologies involving ylides, carbenoid chemistry, metal-mediated cycloaddition reactions, and allylic cyclization methodologies for the synthesis of VCPs are described. Based on the type of VCPs, their reactivity is dealt under electrophile-, radical-, and nucleophile-mediated reactions. Several examples from transition-metal-mediated ring-opening reactions are discussed.

1 Introduction

2 Synthetic Routes to Vinylcyclopropanes

2.1 Ylide Chemistry

2.2 Transition-Metal-Mediated Synthesis

3 Reactivity of Vinylcyclopropanes

3.1 Electrophile-Mediated Ring-Opening Reactions

3.2 Radical-Mediated Ring-Opening Reactions

3.3 Nucleophile-Mediated Ring-Opening Reactions

3.4 Transition-Metal-Mediated Ring-Opening Reactions

4 Conclusion

Key words

vinylcyclopropanes - cyclopropanation - ring opening - ring expansion - radical intermediate - donor–acceptor cyclopropanes

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