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Synthesis 2003(7): 1065-1070
DOI: 10.1055/s-2003-39164
DOI: 10.1055/s-2003-39164
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Phthalimidomethylation of O-Nucleophiles with O-Phthalimidomethyl Trichloroacetimidate: A Powerful Imidomethylating Agent for O-Protection
Further Information
Received
22 January 2003
Publication Date:
09 May 2003 (online)
Publication History
Publication Date:
09 May 2003 (online)
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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