通过α-取代的乙烯基叠氮化物与双环[1.1.0]丁烷的(3 + 2)环化反应模块化合成叠氮双环[2.1.1]己烷。
Modular Synthesis of Azidobicyclo[2.1.1]hexanes via (3 + 2) Annulation of α-Substituted Vinyl Azides and Bicyclo[1.1.0]butanes.
作者信息
Hu Sai, Gao Yuhong, Pan Yuming, Ni Dongshun, Deng Li
机构信息
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang Province 310030, China.
Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang Province 310030, China.
出版信息
J Org Chem. 2024 Oct 18;89(20):15151-15157. doi: 10.1021/acs.joc.4c01920. Epub 2024 Sep 27.
Here, we present a mild and rapid method to access azidobicyclo[2.1.1]hexanes via formal (3 + 2) cycloaddition of α-substituted vinyl azides and bicyclo[1.1.0]butanes under Lewis acid catalysis. A wide range of α-substituted vinyl azides were tolerated under mild conditions. Notably, the resulting cycloadducts could be transformed into structurally attractive 3-azabicyclo[3.1.1]heptenes through microwave-promoted rearrangement. The utilities were highlighted by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of tertiary alkyl azide and further transformation of the azide and ketone groups.
在此，我们展示了一种温和且快速的方法，即在路易斯酸催化下，通过α-取代乙烯基叠氮化物与双环[1.1.0]丁烷的形式上的（3 + 2）环加成反应来制备叠氮双环[2.1.1]己烷。在温和条件下，多种α-取代乙烯基叠氮化物都能被耐受。值得注意的是，通过微波促进的重排反应，所得的环加成产物可以转化为结构吸引人的3-氮杂双环[3.1.1]庚烯。通过叔烷基叠氮化物的铜（I）催化的惠斯根1,3-偶极环加成反应以及叠氮基和酮基的进一步转化突出了其效用。
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