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Synfacts 2005(0): 0080-0080
DOI: 10.1055/s-2005-869882
DOI: 10.1055/s-2005-869882
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
A Polymeric FeCl3 Catalyst for Deprotection of Acetonides
Contributor(s): Yasuhiro Uozumi, Maki MinakawaM. Adharvana Chari*, K. Syamasundar
J. N. T. University, Hyderabad, India
Polymer-Supported Ferric Chloride as a Heterogeneous Catalyst for Chemoselective Deprotection of Acetonides
Synthesis 2005, 708-710
J. N. T. University, Hyderabad, India
Polymer-Supported Ferric Chloride as a Heterogeneous Catalyst for Chemoselective Deprotection of Acetonides
Synthesis 2005, 708-710
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
acetonides - catalysis - diols
Significance
Highly chemoselective deprotection of diacetone sugars bearing various functional groups was achieved at room temperature for 30 minutes using poly(4-vinylpyridine)-supported ferric chloride (5 mol%) to give the corresponding terminal diols 2 in 87-94% yields (15 substrates). This method was found to be of good functional compatibility with acid-sensitive groups such as TBDMS, THP, OBn, OBz, and OAc. The polymeric catalyst was readily recycled without lenching of ferric chloride.
Comment
Several examples of protection/deprotection of 1,2-diols with acetonide using FeCl3 (e.g., A. Fadel, R. Yefsah, J. Salaün Synthesis 1987, 37-39) have been reported so far.