Indium(I) Iodide-Mediated Regioselective Ring Opening of Epoxides with Diphenyldiselenide: The Preparation of β-Hydroxy Selenides

O.   S. do Rego   Barros; A.   B.   de Carvalho; E.   S.   Lang; C.      Peppe

doi:10.2174/1570178043488671

Abstract

Epoxides were efficiently transformed into β-hydroxy selenides by the action of diphenyldiselenide and indium(I) iodide under mild conditions. The ring opening reaction is regioselective with nucleophile incorporation at the less hindered carbon atom for alkyl-substituted epoxides, and at the benzylic carbon atom for aryl derivatives.

Keywords: epoxide, ring opening reaction, indium, hydroxy selenide, regioselectivity

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Letters in Organic Chemistry

Title: Indium(I) Iodide-Mediated Regioselective Ring Opening of Epoxides with Diphenyldiselenide: The Preparation of β-Hydroxy Selenides

Volume: 1 Issue: 1

Author(s): O. S. do Rego Barros, A. B. de Carvalho, E. S. Lang and C. Peppe

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Keywords: epoxide, ring opening reaction, indium, hydroxy selenide, regioselectivity

Abstract: Epoxides were efficiently transformed into β-hydroxy selenides by the action of diphenyldiselenide and indium(I) iodide under mild conditions. The ring opening reaction is regioselective with nucleophile incorporation at the less hindered carbon atom for alkyl-substituted epoxides, and at the benzylic carbon atom for aryl derivatives.

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Barros S. do Rego O., de Carvalho B. A., Lang S. E. and Peppe C., Indium(I) Iodide-Mediated Regioselective Ring Opening of Epoxides with Diphenyldiselenide: The Preparation of β-Hydroxy Selenides, Letters in Organic Chemistry 2004; 1 (1) . https://dx.doi.org/10.2174/1570178043488671