Silver-Catalyzed Diastereo- and Enantioselective Michael Addition and 1,3-Dipolar Cycloaddition Reactions of Imino Esters to 3‑Methyl-4-nitro-5-styrylisoxazoles

The AgOAc/ThioClickFerrophos complex catalyzed conjugate additions and 1,3-dipolar cycloadditions of 3-methyl-4-nitro-5-styrylisoxazoles with 1-pyrroline-5-carboxylates and glycine imino esters to give the corresponding Michael adducts and cycloadducts, respectively, in good yields with excellent di...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-11, Vol.83 (22), p.13965-13972
Main Authors: Kato, Shuma, Suzuki, Yuko, Suzuki, Kota, Haraguchi, Ryosuke, Fukuzawa, Shin-ichi
Format: Article
Language:English
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Summary:The AgOAc/ThioClickFerrophos complex catalyzed conjugate additions and 1,3-dipolar cycloadditions of 3-methyl-4-nitro-5-styrylisoxazoles with 1-pyrroline-5-carboxylates and glycine imino esters to give the corresponding Michael adducts and cycloadducts, respectively, in good yields with excellent diastereo- and enantioselectivities. These reactions can provide pyrroline- or pyrrolidine-containing isoxazole hybrid molecules that have potential biological and pharmaceutical activities.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02309