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Hydrogenolytic cleavage of naphthylmethyl ethers in the presence of sulfides
Philip O Adero1, Dean R Jarois1, David Crich1
1Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA.
Abstract:
With the aid of a series of model thioether or thioglycoside containing polyols protected with combinations of benzyl ethers and 2-naphthylmethyl ethers it is demonstrated that the latter are readily cleaved selectively under hydrogenolytic conditions in the presence of the frequently catalyst-poisoning sulfides. These results suggest the possibility of employing 2-naphthylmethyl ethers in place of benzyl ethers in synthetic schemes when hydrogenolytic deprotection is anticipated in the presence of thioether type functionality.
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