Highly Diastereoselective Synthesis of Trifluoromethylated Spirocyclopropanes from 2-(2'-Ketoalkyl)-1,3-Indandiones and CF3-Imidoyl Sulfoxonium Ylides.
Oct 2026· Journal of Organic Chemistry· 0 citations· 44 references
Medicine
Abstract
A metal-free and highly diastereoselective strategy for the synthesis of trifluoromethylated spirocyclopropanes has been developed using CF3-imidoyl sulfoxonium ylides (TFISYs) and 2-(2'-ketoalkyl)-1,3-indandiones. The transformation proceeds through a base-mediated cascade process to furnish densely functionalized trifluoromethylated spirocyclopropanes in good to excellent yields with excellent diastereoselectivity. The protocol exhibits a broad substrate scope, gram-scale applicability, and synthetic versatility through post-functionalization, providing efficient access to fluorinated spirocyclic architectures of potential medicinal relevance.
The highly enantio- and diastereoselective N-heterocyclic carbene-catalyzed [3 + 2] annulation of isatin-derived enals and α-EWG-functionalized chalcones is disclosed. Developed herein is an efficient, operationally simple, and general synthetic protocol for the straightforward construction of spirocyclopentane oxindol...
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A formal [3+2] cycloaddition of alkynyl diazoketones with aminomalonates has been developed, providing rapid access to highly substituted γ,γ-disubstituted 3-pyrrolin-2-ones. This transformation proceeds under mild conditions with broad substrate scope and good functional-group tolerance, providing a practical approach...
Xin Ji, Ying-Wen Dai, Shu-Yu Yao et al.· Chemistry· 0 citations
A series of substituted tetrahydroquinoline (THQ) derivatives were synthesized via a triflic acid-promoted multicomponent aza-Prins-Ritter reaction of 2-(tosylamino)styrenes with carbonyl compounds and substituted acetonitriles, the latter serving as both solvent and nucleophile. The reaction proceeds under mild condit...
Afton Fults, Moh. Sattar, Sakamuri Sarath Babu et al.· Journal of Organic Chemistry· 0 citations
A novel ruthenium(II)-catalyzed, oxo-directed C5-H acylmethylation of 2-arylquinolin-4(1H)-ones with sulfoxonium ylides has been developed. Weak carbonyl coordination overrides the competing nitrogen center, providing excellent C5 selectivity. The procedure shows excellent tolerance of functional groups, a broad substr...
Ajay Kant Gola, S. Pandey· Chemical Communications· 0 citations
Herein, a variety of spirochromeno[4,3-b][1,3]pyrrole-cyclopropanes bearing four contiguous stereocenters were prepared in moderate to good yields with high diastereoselectivity through copper(I)-catalyzed 2,3-rearrangement-driven cyclopropanation of O-propargylic oximes with sulfur ylides. Mechanistic studies revealed...
Despite the relevance of 2-imino-3-spiroindoles, particularly in medicinal chemistry, their synthesis still relies on highly reactive coupling partners. Herein, a novel approach to 2-imino-3-spiroindoles, involving the BF3-catalyzed Diels-Alder reaction of α,β-unsaturated iminoindoles with substituted dienes, is presen...
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