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Keywords = α-amido sulfones

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11 pages, 2055 KB  
Article
Asymmetric Organocatalytic Mannich Reaction in the Synthesis of Hybrid Isoindolinone-Pyrazole and Isoindolinone-Aminal from Functionalized α-Amidosulfone
by Antonia Di Mola, Felice De Piano, Lorenzo Serusi, Giovanni Pierri, Laura Palombi and Antonio Massa
Int. J. Mol. Sci. 2023, 24(6), 5783; https://doi.org/10.3390/ijms24065783 - 17 Mar 2023
Cited by 2 | Viewed by 2699
Abstract
The investigation of the reactivity of an α-amido sulfone derived from 2-formyl benzoate under organocatalytic conditions in the presence of acetylacetone allowed the synthesis of a new heterocyclic hybrid isoindolinone-pyrazole with high enantiomeric excess. Dibenzylamine was also used as a nucleophile to afford [...] Read more.
The investigation of the reactivity of an α-amido sulfone derived from 2-formyl benzoate under organocatalytic conditions in the presence of acetylacetone allowed the synthesis of a new heterocyclic hybrid isoindolinone-pyrazole with high enantiomeric excess. Dibenzylamine was also used as a nucleophile to afford an isoindolinone with aminal substituent in 3-position in suitable selectivity. The use of Takemoto’s bifunctional organocatalyst not only led to observed enantioselectivity but was also important in accomplishing the cyclization step in both cases. Notably, this catalytic system proved to be particularly effective in comparison to widely used phase transfer catalysts. Full article
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9 pages, 627 KB  
Article
Catalytic Enantioselective Cyclopropylalkynylation of Aldimines Generated In Situ from α-Amido Sulfones
by Alicia Monleón, Gonzalo Blay and José R. Pedro
Molecules 2022, 27(12), 3763; https://doi.org/10.3390/molecules27123763 - 11 Jun 2022
Cited by 1 | Viewed by 2066
Abstract
A convenient procedure of synthesis of N-carbamoyl-protected propargylic amines substituted with a cyclopropyl group from α-amido sulfones and cyclopropylacetylene is described. The reaction is catalyzed by a chiral BINOL-type zinc complex and provides the corresponding products in good yields and enantioselectivities. Full article
(This article belongs to the Special Issue Advances in Alkyne Chemistry)
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