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Cycloaddition Reactions of Sugar-Based Olefins, Nitrones and Nitrile Oxides: En Route to Saccharidic Spiroisoxazoli(di)nes

  • Nadia Pellegrini-MoïseEmail author
  • Mylène RichardEmail author
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Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 57)

Abstract

Isoxazoline- and isoxazolidine-containing compounds are privileged structures of interest, notably in synthetic and medicinal chemistry. These heterocycles can be obtained by 1,3-dipolar cycloaddition reactions between an olefin and a nitrile oxide or a nitrone. This reaction generates one C–C and one C–O bond and up to three chiral centres in one step. In the present chapter, we aim to summarize and discuss reports of these cycloadditions on sugar olefins, with a focus on exo-methylene sugars or activated exo-glycals, leading to saccharidic spiroisoxazoli(di)nes with high regio- and stereocontrol. Additional examples of cycloaddition reactions involving chiral nitrone, sugar nitrile oxide, sugar nitrone and two chiral sugar partners will also be discussed. Due to the importance of the spiro structure in several biologically active compounds, these spiroheterocycles can be regarded as spironucleoside analogues, mimics of natural building blocks or multicyclic sugar scaffolds suitable for selective derivatization. Some of them thus showed promising biological properties as antibacterial agents or enzyme inhibitors. Moreover, the labile nature of the N–O bond in the isoxazolidine ring makes it an attractive target for synthetic chemists. The reactivity of this scaffold has therefore been widely studied, and the cycloadducts have been converted to other classes of compounds of interest. Examples of the biological relevance and synthetic use and reactivity of these spiro-sugars will be given in this chapter.

Keywords

Cycloaddition Nitrile oxides Nitrones Spiroisoxazoli(di)nes Sugar-based olefins 
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© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Université de Lorraine-CNRS, UMR 7053 L2CMNancyFrance

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