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

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

References

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