Add time:08/16/2019 Source:sciencedirect.com
Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1,2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1,3-dioxolan-2-ylium cations 8. Subsequent ring-opening via SN2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1,3-diol was employed, furan-containing ester 9 was formed instead of the standard product through an apparent aldol dimerization/fragmentation pathway.
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