A convenient strategy for the synthesis of isoxazole-containing α-CF(3)-substituted α-aminocarboxylates and α-aminophosphonates have been developed. The method is based on copper-catalyzed 1,3-dipolar cycloaddition of different aromatic nitrile oxides to functionalized acetylenes.

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http://dx.doi.org/10.1039/c1ob06040fDOI Listing

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Enantioselective synthesis of isoxazole-containing spirooxindole tetrahydroquinolines squaramide-catalysed cascade reactions.

Org Biomol Chem

July 2022

Key Laboratory of Medical Molecule Science & Pharmaceutics Engineering (Ministry of Industry and Information Technology), School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No.5 Zhongguancun South Street, Beijing 100081, People's Republic of China..

A class of -sulfonylaminostyryl isoxazole synthons were designed and demonstrated to be useful building blocks in asymmetric cascade aza-Michael/Michael reaction with 3-olefinic oxindoles. This squaramide-catalysed cascade reaction afforded structurally complex isoxazole-containing spirooxindole tetrahydroquinolines bearing three contiguous stereocenters in good to excellent yields (up to 99%) with high diastereoselectivities (up to >20 : 1 dr) and enantioselectivities (up to 88% ee). Moreover, the gram-scale synthesis and synthetic transformations were also demonstrated.

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