Phthalimidomethylation of O-Nucleophiles with O-Phthalimidomethyl Trichloroacetimidate: A Powerful Imidomethylating Agent for O-Protection

Ibrahim A. I. Ali; Adel A.-H. Abdel-Rahman; El Sayed H. El Ashry; Richard R. Schmidt

doi:10.1055/s-2003-39164

PAPER

Phthalimidomethylation of O-Nucleophiles with O-Phthalimidomethyl Trichloroacetimidate: A Powerful Imidomethylating Agent for O-Protection

Ibrahim A. I. Ali^a, Adel A.-H. Abdel-Rahman^a, El Sayed H. El Ashry^b, Richard R. Schmidt*^a
^a Department of Chemistry, University of Konstanz, Fach M 725, 78457 Konstanz, Germany
e-Mail: Richard.Schmidt@uni-konstanz.de ;
^b Department of Chemistry, Faculty of Science, University of Alexandria, Alexandria, Egypt
e-Mail: eelashry@link.net or eelashry60@hotmail.com ;

Abstract

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Abstract

Phthalimidomethylation of oxygen nucleophiles by using O-phthalimidomethyl (Pim) trichloroacetimidate in the presence of TMSOTf has been achieved in high yields. Hydrazinolysis of the phthalimido group from the O-derivatives leads to the hydroxy precursors. Thus a convenient method for the protection of oxygen nucleophiles is provided, which complements the repertoire of available hydroxy protecting groups.

Key words

imides - alcohols - aminomethylations - phthalimide - nucleophiles - protecting groups

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References

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