ArticleNature communications2019
Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- IronChemical science · 2024Article
- Further developments ofiScience · 2022Review
- Chiral-at-Iron Catalyst for Highly Enantioselective and Diastereoselective Hetero-Diels-Alder Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindolesChemical science · 2020Article
- H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.Chemical science · 2020Article
- Nickel-Catalyzed Amidoalkylation Reaction of γ-Hydroxy Lactams: An Access to 3-Substituted Isoindolinones.ACS omega · 2019Article
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Authors and funding
4 authors.
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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.
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