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| SHORTPAPER | Synthesis 2004: 1563-1565
DOI: 10.1055/s-2004-822406 |
© Georg Thieme Verlag Stuttgart · New York
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A New and Efficient Epoxide Ring Opening via Poor Nucleophiles: Indole, p-Nitroaniline, Borane and O-Trimethylsilylhydroxylamine in Lithium Perchlorate
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| Akbar Heydari*a, Morteza Mehrdadb, Aziz Malekia, Nafiseh Ahmadia |
a Chemistry Department, Tarbiat Modarres University, P. O. Box 14155-4838, Tehran, Iran
Fax: +98(21)8006544; e-Mail: akbar.heydari@gmx.de;
b Department of Phytochemistry, Shahid Beheshti University, Evin 1983963113, Tehran, Iran
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Received
23 February 2004 |
Abstract
Highly regioselective ring opening of 2,3-dimethyloxirane, 2-epoxyphenylether and allyl(2-epoxymethyl) ether are observed through reactions with poor nucleophiles such as indole, borane, O-trimethylsilylhydroxylamine, p-nitroaniline and sterically hindered tert-butylamine in the presence of 5.0 M lithium perchlorate-Et2O solution. These reactions are fast, convenient, with rather high yields and are carried out at ambient temperatures. Key words
lithium perchlorate - epoxide - β-amino alcohols
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