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PHOTOCHEMISTRY

A light touch for complex products

Nature Chemistry volume 12, pages 889–890 (2020)Cite this article

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The [2+2] photocycloaddition of two double-bond moieties is arguably the most efficient way to form a four-membered ring, but this route is rarely used to construct azetidine rings. Now, the development of an isoxazoline carboxylate cycloaddition partner offers a general approach to synthesize diverse azetidine products.

As azetidines are of considerable interest in agrochemistry and medicinal chemistry2, methods for simple and direct access to these compounds are highly sought after. To promote azetidine formation, cyclic imine derivatives (which cannot undergo E–Z isomerization) have been used, but the imine partners chosen yielded azetidine products that are not amenable to further derivatization, and thus only a narrow range of azetidine products was accessible. Now, writing in Nature Chemistry, Corinna Schindler and colleagues have developed a broadly applicable aza-Paternò–Büchi process, promoted by visible light, that enables the preparation of diverse azetidine products by using an isoxazoline carboxylate cycloaddition partner3 (Fig. 1c).

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Fig. 1: The development of a broadly applicable protocol for intermolecular aza-Paternò–Büchi reactions to generate diverse azetidine products.

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  1. Department of Chemistry, Lancaster University, Lancaster, UK

    Susannah Coote

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  1. Susannah Coote
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Correspondence to Susannah Coote.

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Coote, S. A light touch for complex products. Nat. Chem. 12, 889–890 (2020). https://doi.org/10.1038/s41557-020-0536-y

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