Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides

Nuligonda Thirupathi, Fang Wei, Chen-Ho Tung and Zhenghu Xu ()
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Nuligonda Thirupathi: Shandong University
Fang Wei: Shandong University
Chen-Ho Tung: Shandong University
Zhenghu Xu: Shandong University

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract Vinyl azides, bearing conjugated azide and alkene functional groups, have been recognized as versatile building blocks in organic synthesis. In general vinyl azides act as 3-atom (CCN) synthons through the fast release of molecular nitrogen and have been extensively utilized in the construction of structurally diverse N-heterocycles. Keeping the azide moiety intact in organic transformations to synthesis chiral azides is an important but challenging task. Herein, we report an enantioselective copper(II)/BOX-catalyzed cycloaddition of vinyl azides, generating diverse chiral cyclic azides. α-Aryl substituted vinyl azides react with unsaturated keto esters through an inverse-electron-demand hetero-Diels-Alder reaction to afford chiral azido dihydropyrans with excellent enatioselectivities. In contrast, cyclohexenyl azides undergo a diastereo- and enantio-selective Diels-Alder reaction giving important azido octahydronaphthalenes with three continuous stereogenic centers. Notable features of these reactions include a very broad scope, mild reaction conditions and 100% atom economy.

Date: 2019
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DOI: 10.1038/s41467-019-11134-8

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