Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 42, Pages 15041-15045Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907269
Keywords
carboamination; C-H activation; diastereoselectivity; dienes; multicomponent reactions
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Funding
- Deutsche Forschungsgemeinschaft (Leibniz Award) [SFB 858]
- WWU Munster (Graduate School of Molecules and Interfaces)
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A protocol for the three-component 1,4-carboamination of dienes is described. Synthetically versatile Weinreb amides were coupled with 1,3-dienes and readily available dioxazolones as the nitrogen source using [Cp*RhCl2](2)-catalyzed C-H activation to deliver the 1,4-carboaminated products. This transformation proceeds under mild reaction conditions and affords the products with high levels of regio- and E-selectivity. Mechanistic investigations suggest an intermediate Rh-III-allyl species is trapped by an electrophilic amidation reagent in a redox-neutral fashion.
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