Zirconium Tetrachloride (ZrCl4) as an Efficient and Chemoselective Catalyst for Conversion of Carbonyl Compounds to 1,3-Oxathiolanes

Babak Karimi; Hassan Seradj

doi:10.1055/s-2000-6692

Synlett 2000; 2000(6): 0805-0806
DOI: 10.1055/s-2000-6692

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Zirconium Tetrachloride (ZrCl₄) as an Efficient and Chemoselective Catalyst for Conversion of Carbonyl Compounds to 1,3-Oxathiolanes

Babak Karimi^* , Hassan Seradj

^*Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P. O. Box 45195-159, Gava Zang, Zanjan, Iran; Fax +98(0241)449023; E-mail: karimi@iasbs.ac.ir

Abstract

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Different types of aldehydes and ketones can be efficiently converted into their corresponding 1,3-oxathiolanes using 2-mercaptoethanol (1.5 - 3.2 equiv.) in the presence of catalytic amount (0.04 - 0.15 equiv.) of ZrCl₄ in CH₂Cl₂ as solvent at room temperature. Chemoselective monothioacetalization of aldehydes in the presence of ketones can also be achieved in high yield. The work-up is easy and removal of water is not necessary.

acetals - 1,3-oxathiolanes - protecting groups - zirconium tetrachloride - O,S-acetals

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