Esterification and Etherification of Aliphatic Alcohols Enabled by Catalytic Strain-Release of Donor-Acceptor Cyclopropane

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Org Lett. 2024 Jun 6. doi: 10.1021/acs.orglett.4c01637. Online ahead of print.

ABSTRACT

We herein disclose a highly efficient protocol for the esterification and etherification of alcohols, leveraging a Sc(OTf)3-catalyzed ring-strain release event in the meticulously designed, chromatographically stable mixed anhydrides or benzyl esters that incorporate an intramolecular donor-acceptor cyclopropane (DAC). This versatile method facilitates the straightforward functionalization of sugar, terpene, and steroid alcohols under mild acidic conditions, as showcased by the single-catalyst-driven, dual protection of sugar diol.

PMID:38842488 | DOI:10.1021/acs.orglett.4c01637