ZrCl4 as an efficient catalyst for a novel one-pot protection/deprotection synthetic methodology.

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.