A New and Efficient Epoxide Ring Opening via Poor Nucleophiles: Indole, p-Nitroaniline, Borane and O-Trimethylsilylhydroxylamine in Lithium Perchlorate

Akbar Heydari*, Morteza Mehrdad, Aziz Maleki, Nafiseh Ahmadi

*Chemistry Department, Tarbiat Modarres University, P. O. Box 14155-4838, Tehran, Iran, Email: akbar.heydarigmx.de

A. Heydari, M. Mehrdad, A. Maleki, N. Ahmadi, Synthesis, 2004, 1557-1558.

DOI: 10.1055/s-2004-822406

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Abstract

Highly regioselective ring opening of epoxides with poor nucleophiles such as indole, borane, O-trimethylsilylhydroxylamine, p-nitroaniline and sterically hindered tert-butylamine is a fast and convenient reaction in the presence of 5.0 M lithium perchlorate-Et₂O solution (LPDE).

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Key Words

lithium perchlorate, epoxide (reduction), β-amino alcohols, hydroxylamines, borane

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ID: J66-Y2004-2130