Intermolecular direct catalytic cross-Michael/Michael reactions and tandem Michael/Michael/aldol reactions to linear compounds

Catalytic cross-Michael/Michael reactions of nitroalkenes and ethyl acrylate with pronucleophiles including thiols, dimethyl methylmalonate, and 2-nitropropane to linear three-component products were developed by using a catalytic amount of DBU in DMSO. Tandem sulfa-Michael/Michael/aldol reactions o...

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Bibliographic Details
Published in:Tetrahedron 2022-09, Vol.122, p.132951, Article 132951
Main Authors: Asaji, Yuta, Maruyama, Hibiki, Yoshimura, Tomoyuki, Matsuo, Jun-ichi
Format: Article
Language:English
Subjects:
Aldol reaction
Catalytic reaction
Michael reaction
Multi-component reaction
Tandem reaction
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Summary:Catalytic cross-Michael/Michael reactions of nitroalkenes and ethyl acrylate with pronucleophiles including thiols, dimethyl methylmalonate, and 2-nitropropane to linear three-component products were developed by using a catalytic amount of DBU in DMSO. Tandem sulfa-Michael/Michael/aldol reactions of a thiol, a nitroalkene, ethyl acrylate, and an aldehyde proceeded to give a linear four-component product. The high nucleophilicity of in situ-formed nitronate anions and ester enolates in DMSO was important for the present multi-component cascade reactions using pronucleophiles that had protons with relatively high acidity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.132951