The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Palladium-Catalyzed [3 + 2] Cycloaddition via Twofold 1,3-C(sp3)-H Activation, the main research direction is palladium catalyzed cycloaddition carbon hydrogen bond activation; amide lactam cycloaddition maleimide.Category: isothiazole.
Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) is required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3 + 2] reaction that utilizes twofold C(sp3)-H activation to generate the three-carbon unit for formal cycloaddition The initial β-C(sp3)-H activation of aliphatic amide, followed by maleimide insertion, triggers a relayed, second C(sp3)-H activation to complete a formal [3 + 2] cycloaddition The key to success was the use of weakly coordinating amide as the directing group, as previous studies have shown that Heck or alkylation pathways are preferred when stronger-coordinating directing groups are used with maleimide coupling partners [e.g., N,N-dimethylpivalamide + N-(4-nitrophenyl)maleimide → I (87%, dr 6:1)]. To promote the amide-directed C(sp3)-H activation step, the use of pyridine-3-sulfonic acid ligands is crucial. This method is compatible with a wide range of amide substrates, including lactams, which lead to spiro-bicyclic products. The [3 + 2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.
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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com