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29.18.1.1.3 Method 3: Synthesis from 1-Acyloxy-1-hydroxy Compounds, Carbonyl Hydrates, or Vinyl Esters

DOI: 10.1055/sos-SD-129-00201

Smith, L. H. S.; Coote, S. C.; Procter, D. J.Science of Synthesis Knowledge Updates, (20103482.

1-Acyloxy-1-hydroxy compounds (“hemiacylals”) are generally cyclic species that can be acylated under basic or acidic conditions. Alternatively, the hydroxy group can be activated as a leaving group by formation of a sulfonate ester and then displaced with a carboxyl nucleophile. Enantioselective methods have also been developed. Carbonyl hydrates and vinyl esters have also been converted into acylals under acidic conditions.

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References


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