1,2-Diarylethanols by Alternative Regioselective Reductive Ring-Opening of 2,3-Diaryloxiranes
| Autor: | Nadia Di Blasio, Maria Teresa Lopardo, Paolo Lupattelli |
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| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
Chemistry
Aryl Organic Chemistry Regioselectivity ring-opening reactions reductions Ring (chemistry) Medicinal chemistry alcohols chemistry.chemical_compound epoxides regioselectivity enantioselectivity Structural isomer Organic chemistry Physical and Theoretical Chemistry Enantiomeric excess Catalytic hydrogenation Electronic properties |
| Popis: | Non-symmetrical trans-2,3-diaryloxiranes have been regioselectively opened by catalytic hydrogenation over Pd/C, NaBH4/Pd and [Cp2TiCl]/H2O. Although in the catalytic hydrogenation reactions the epoxides were mainly opened at the β-carbon with respect to the substituted aryl ring in all cases, with the [Cp2TiCl]/H2O system the regioselectivity was affected by the electronic properties of the aryl residues, the epoxides being opened on the carbon bearing the most electron-releasing or the least electron-withdrawing group. With the NaBH4/Pd system different regioisomers were obtained depending on the substituents. Starting from enantioenriched epoxides, no loss of optical purity was observed in the alcohols formed.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) |
| Databáze: | OpenAIRE |
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