Acyloin

In organic chemistry, acyloins or α-hydroxy ketones[1] are a class of organic compounds of the general form R−C(O)CH(OH)−R', composed of a hydroxy group (−OH) adjacent to a ketone group (>C=O).

Classic organic reactions exist for the synthesis of acyloins.

When sulfonyloxaziridines oxidize enol(ate)s, the latter reacts by nucleophilic displacement at the electron deficient oxygen of the oxaziridine ring.

This modification is applied in the Holton taxol total synthesis.

In the enolate oxidation of the cyclopentadienone below[5] with either camphor enantiomer, the trans isomer is obtained because access for the hydroxyl group in the cis position is limited.