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
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
ID: J66-Y2004-2130