Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, IL, USA.
Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11579-11583. doi: 10.1002/anie.201705681. Epub 2017 Aug 9.
An electrocyclization route to azetidine nitrones from N-alkenylnitrones was discovered that provides facile access to these unsaturated strained heterocycles. Reactivity studies showed that these compounds undergo a variety of reduction, cycloaddition, and nucleophilic addition reactions to form highly substituted azetidines with excellent diastereoselectivity. Taken together, these transformations provide a fundamentally different approach to azetidine synthesis than traditional cyclization by nucleophilic displacement and provide novel access to a variety of underexplored strained heterocyclic compounds.
我们发现了一种由 N-烯基硝酮生成氮杂环丁烷硝酮的电环化途径，该途径可方便地得到这些不饱和张力杂环。反应性研究表明，这些化合物经历了多种还原、环加成和亲核加成反应，以形成具有极好的非对映选择性的高度取代的氮杂环丁烷。总的来说，这些转化为氮杂环丁烷的合成提供了一种与传统的亲核取代环化完全不同的方法，并为各种未充分探索的张力杂环化合物提供了新的途径。
