Volume 27, Issue 23
Natural Products
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ChemInform Abstract: Hydride Addition to 1,2-Anhydrosugars: A Highly Stereoselective Route to Anhydroalditols.

T. M. FLAHERTY

T. M. FLAHERTY

Dep. Chem., Univ. Ariz., Tucson, AZ 85721, USA

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J. GERVAY

J. GERVAY

Dep. Chem., Univ. Ariz., Tucson, AZ 85721, USA

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First published: June 4, 1996

Abstract

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ChemInform Abstract

The stereoselective hydride addition reaction to the 1,2-anhydrosugar ( I) is investigated under different reaction conditions. Surprisingly Lewis acid catalyzed addition of triethylsilane gives only the unwanted diol (III) (conditions A) or low yield of (II) (conditions B). However, direct reduction with lithium aluminium hydride yields the desired (II) exclusively.

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