期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 38, 页码 11579-11583出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705681
关键词
4 pi-electrocyclization; azetidines; Chan-Lam reaction; nitrones; strained heterocycles
资金
- National Science Foundation [NSF-CHE 1464115]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1464115] Funding Source: National Science Foundation
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 diastereo-selectivity. 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.
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