Synthesis of Differentially
Protected myo- and chiro-Inositols
from d-Xylose: Stereoselectivity in Intramolecular
SmI2-Promoted Pinacol Reactions

Giovanni Luchetti; Kejia Ding; Alexander Kornienko; Marc d’Alarcao

doi:10.1055/s-2008-1067259

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Synthesis 2008(19): 3148-3154
DOI: 10.1055/s-2008-1067259

SPECIALTOPIC

Synthesis of Differentially Protected myo- and chiro-Inositols from d-Xylose: Stereoselectivity in Intramolecular SmI₂-Promoted Pinacol Reactions

Giovanni Luchetti^a, Kejia Ding^b, Alexander Kornienko*^a, Marc d’Alarcao*^b
^a Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA
Fax: +1(575)8355364; e-Mail: akornien@nmt.edu;
^b Department of Chemistry, San José State University, San José, CA 95192-0101, USA
Fax: +1(408)9244945; e-Mail: mdalarcao@science.sjsu.edu;

Further Information

Publication History

Received 20 May 2008
Publication Date:
05 September 2008 (online)

Abstract
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Abstract

Methods for the enantioselective conversion of d-xylose into differentially protected myo-inositol and l-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI₂-promoted pinacol coupling. The stereoselectivity was extremely dependent on the conditions, suggesting a change in mechanism. Preliminary mechanistic experiments and possible explanations for this behavior are discussed.

Key words

inositol - pinacol - samarium - stereoselective - carbohydrates

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