Abstract

Hypervalent iodine reagents have been developed as highly valuable reagents in synthetic organic chemistry during the past few decades. These reagents have been identified as key replacements of various toxic heavy metals in organic synthesis. Various synthetically and biologically important scaffolds have been developed using hypervalent iodine reagents either in stoichiometric or catalytic amounts. In addition, hypervalent iodine reagents have been employed for the synthesis of spirocyclic scaffolds via dearomatization processes. In this review, various approaches for the synthesis of spirocyclic scaffolds using hypervalent iodine reagents are covered including their stereoselective synthesis. Additionally, the applications of these reagents in natural product synthesis are also covered.

Highlights

  • The chemistry of spirocyclic compounds is a well established research area of organic and medicinal chemistry [1,2,3,4,5]

  • Active hypervalent iodine species was generated in situ by the oxidation of bis(iodoarene) 25 using m-chloroperbenzoic acid (mCPBA) as terminal oxidant

  • 2 mol % of bis(iodoarene) 81 was used as precatalyst and peracetic acid (PAA) as an oxidant instead of mCPBA, which plays an important role in generation of active iodine(III) species

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Summary

Introduction

The chemistry of spirocyclic compounds is a well established research area of organic and medicinal chemistry [1,2,3,4,5]. Hypervalent iodine reagents provide various functional group transformation opportunities in organic chemistry Their environment-friendly nature and mild reaction conditions makes them more attractive candidates for the replacements of various toxic metals in organic synthesis [18,19,20,21,22,23,24,25,26,27,28,29,30,31]. Both heterocyclic and carbocyclic spirocyclic compounds can be achieved using these reagents [27,32]

Synthesis of spirolactones
Synthesis of spirolactams
Synthesis of spirocarbocycles
Synthesis of miscellaneous spirocyclic compounds
Findings
Conclusion
Full Text
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