ZrCl4 as an efficient catalyst for a novel one-pot protection/deprotection synthetic methodology |
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Authors: | Singh Surendra Duffy Colm D Shah Syed Tasadaque A Guiry Patrick J |
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Affiliation: | Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland |
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Abstract: | A catalytic quantity of ZrCl 4 (20 mol %) was found to be an efficient catalyst for the one-pot esterification and deprotection of (5 S,6 R)-5,6-diacetoxyoct-7-enoic acid in good yields (44-62%) with a lactone formed as a minor byproduct. ZrCl 4 (10-20 mol %) was also sufficient to deprotect 1,3-dioxalane, bis-TBDMS ethers, and diacetate functional groups in excellent yields of up to 93%. ZrCl 4 (1-10 mol %) also promoted diol protection as the acetonide in 90% yield and acted as a trans-esterification catalyst for a range of esters. |
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