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Highly enantioselective synthesis of beta-amidophenylthioethers by organocatalytic desymmetrization of meso-aziridines. 2009

Giorgio Della Sala, and Alessandra Lattanzi
Department of Chemistry, University of Salerno, Via Ponte Don Melillo 8, 84024 Fisciano (SA), Italy. gdsala@unisa.it

The desymmetrization of N-acylaziridines with Me(3)SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.

UI MeSH Term Description Entries
D010616 Phenanthrenes POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.
D001388 Aziridines Saturated azacyclopropane compounds. They include compounds with substitutions on CARBON or NITROGEN atoms. Ethyleneimines,Azacyclopropanes, Saturated,Dimethyleneimines,Saturated Azacyclopropanes
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013440 Sulfides Chemical groups containing the covalent sulfur bonds -S-. The sulfur atom can be bound to inorganic or organic moieties. Sulfide,Thioether,Thioethers,Sulfur Ethers,Ethers, Sulfur

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