Catalytic Asymmetric Ring Opening Reactions of Vinylcyclopropanes

Vinylcyclopropanes can be generally classified as activated and unactivated VCPs. Activated VCPs have strong electron withdrawing groups present in the cyclopropane ring, while unactivated VCPs lack strong electron withdrawing groups in their structures. These VCPs can be activated using suitable asymmetric catalysts to afford various types of chiral ring-opened products that are synthetically valuable compounds.

Abstract

Vinylcyclopropanes (VCPs) are important building blocks with multifaceted reactivity. Catalytic asymmetric ring opening of vinylcyclopropanes is a highly efficient process to access valuable chiral molecules with diverse functionalities that can be further functionalized for a series of synthetic purposes. VCPs are very well-known substrates for cycloaddition reactions and this chemistry has been widely explored. On the contrary, despite of enormous synthetic potential, development of new innovative strategies for the catalytic, asymmetric ring opening of VCPs is somewhat underdeveloped. Recently, several significant examples have emerged in the literature for various asymmetric ring opening of both activated and unactivated vinylcyclopropanes that involve transition metal catalysis. These developments are relevant additions to the vinylcyclopropane chemistry. In this review, we aim to summarize all the catalytic asymmetric ring opening transformations reported till date and provide a comprehensive analysis of these research outcomes.

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