Synthesis 2016; 48(24): 4347-4380
DOI: 10.1055/s-0035-1562530
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in the Synthesis and Reactivity of Vinylcyclopropanes

Venkataraman Ganesh
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India   Email: [email protected]
,
Srinivasan Chandrasekaran*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 11 May 2016

Accepted after revision: 05 July 2016

Publication Date:
09 September 2016 (online)


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

 
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