Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 23, Pages 5964-5968Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201400885
Keywords
cycloadditions; cyclopropanes; heterocycles; nitrosoarene; stereoselective synthesis
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Funding
- DFG
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The MgBr2-catalyzed formal [3+2] cycloaddition of donor-acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity. Product isoxazolidines can be readily transformed into a-amino lactones by reductive or decarboxylative N-O cleavage and subsequent lactonisation, and the N-aryl bond cleavage is also possible under oxidative conditions.
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