Acetal formation by solvolysis of glucal-derived donor-acceptor cyclopropanes |
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| Authors: | Ming YuBrian L Pagenkopf |
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| Institution: | Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712, USA |
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| Abstract: | The conversion of glucal derived donor-acceptor cyclopropanes to acetals by TiCl4 mediated ring opening and alcohol trapping is described. Good selectivity for the alpha anomer and yields near 90% are consistently observed with aliphatic, benzylic and allylic alcohols, phenols and thiophenols. The utility of this method to prepare oligosaccharides through intermediate O,S-acetals is illustrated. |
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| Keywords: | cyclopropanes enzyme inhibitors solvolysis |
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