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.

1,2-Diarylethanols by Alternative Regioselective Reductive Ring-Opening of 2,3-Diaryloxiranes / Lupattelli, Paolo; LOPARDO M., T; DI BLASIO, N.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - (2009), pp. 938-944. [10.1002/ejoc.200800992]

1,2-Diarylethanols by Alternative Regioselective Reductive Ring-Opening of 2,3-Diaryloxiranes

LUPATTELLI, Paolo;
2009

Abstract

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.
2009
epoxides; ring-opening reactions; reductions; alcohols; enantioselectivity; regioselectivity
01 Pubblicazione su rivista::01a Articolo in rivista
1,2-Diarylethanols by Alternative Regioselective Reductive Ring-Opening of 2,3-Diaryloxiranes / Lupattelli, Paolo; LOPARDO M., T; DI BLASIO, N.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - (2009), pp. 938-944. [10.1002/ejoc.200800992]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1653073
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