标题:Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides
作者:Thirupathi, Nuligonda; Wei, Fang; Tung, Chen-Ho; Xu, Zhenghu
作者机构:[Thirupathi, Nuligonda; Wei, Fang; Tung, Chen-Ho; Xu, Zhenghu] Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Minist Educ, 27 更多
通讯作者:Xu, ZH;Xu, ZH
通讯作者地址:[Xu, ZH]Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Minist Educ, 27 South Shanda Rd, Jinan 250100, Shandong, Peoples R Chin 更多
来源:NATURE COMMUNICATIONS
出版年:2019
卷:10
DOI:10.1038/s41467-019-11134-8
摘要: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. alpha-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.
收录类别:SCOPUS;SCIE
资源类型:期刊论文
原文链接:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85069468192&doi=10.1038%2fs41467-019-11134-8&partnerID=40&md5=5e5b6271224e4a6b79feec525274875a
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