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Synfacts 2005(0): 0080-0080  
DOI: 10.1055/s-2005-869882
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Polymeric FeCl3 Catalyst for Deprotection of Acetonides

Rezensent(en): Yasuhiro Uozumi, Maki Minakawa
M. 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  
Thieme Connect
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Publikationsdatum:
20. Juli 2005 (online)

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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.

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