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- Title
α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric exo-Selective 1,3-Dipolar Cycloaddition with Nitrones.
- Authors
Zhang, Ming; Kumagai, Naoya; Shibasaki, Masakatsu
- Abstract
1,3-Dipolar cycloaddition is a commonly exploited method to access 5-membered chemical entities with a variety of peripheral functionalities and their stereochemical arrangements. Nitrones are isolable 1,3-dipoles that exhibit sufficient reactivity toward electron-deficient olefins in the presence of Lewis acids to deliver highly substituted isoxazolidines. Herein we document that α,β-unsaturated amides, generally regarded as barely reactive in a 1,3-dipolar reaction manifold, were effectively activated using the designed 7-azaindoline auxiliary in an In(OTf)3/bishydroxamic acid catalytic system. The broad substrate scope and clean removal of the 7-azaindoline auxiliary from the product highlight the synthetic utility of the present catalysis.
- Subjects
AMIDE synthesis; NITRONE derivatives; SUBSTITUENTS (Chemistry); RING formation (Chemistry); AMIDE derivatives; REACTIVITY (Chemistry); STEREOCHEMISTRY
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 51, p12450
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201702330