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Acyloins are a class of organic compounds in organic chemistry sharing a common functional group consisting of a hydroxyl group placed on the α-position of a carbonyl group.
Additional recommended knowledge
Synthesis of acyloins
Classic organic reactions exist for the synthesis of acyloins.
Enolate oxidation by sulfonyloxaziridines
Enolates can be oxidized by sulfonyloxaziridines  . The enolate reacts by nucleophilic displacement at the electron deficient oxygen of the oxaziridine ring.
This reaction type is extended to asymmetric synthesis by the use of chiral oxaziridines derived from camphor (camphorsulfonyl oxaziridine). Each isomer gives exclusive access to one of the two possible enantiomers. This modification is applied in the Holton Taxol total synthesis.
In the enolate oxidation of the cyclopentaenone below  with either camphor enantiomer the trans isomer is obtained because access for the hydroxyl group in the cis position is limited. The use of the standard oxaziridine did not result in an acyloin.
Reactions of acyloins
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Acyloin". A list of authors is available in Wikipedia.|