ZrCl4 as an Efficient Catalyst for a Novel One-Pot Protection/Deprotection Synthetic Methodology
A catalytic quantity of ZrCl4 (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. ZrCl4 (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%. ZrCl4 (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.
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. ZrCl4 (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%. ZrCl4 (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.
A catalytic quantity of ZrCl4 (20 mol %) was found to be an efficient catalyst for the one-pot esterification and deprotection of (5S,6R)-5,6-diacetoxyoct-7-enoic acid in good yields (44−62%) with a lactone formed as a minor byproduct. ZrCl4 (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%. ZrCl4 (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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