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Acyloin



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.

 

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Synthesis of acyloins

Classic organic reactions exist for the synthesis of acyloins.

Enolate oxidation by sulfonyloxaziridines

Enolates can be oxidized by sulfonyloxaziridines [1] [2]. 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 [3] 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

References

  1. ^  Synthesis of .alpha.-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2 sulfonyloxaziridines Franklin A. Davis, Lal C. Vishwakarma, Joanne G. Billmers, John Finn J. Org. Chem.; 1984; 49(17); 3241-3243. Abstract
  2. ^  Asymmetric Oxidation of Ester and Amide Enolates Using New (Camphorylsulfony1)oxaziridines Davis, F. A.; Haque, M. S.; Ulatowski, T. G.; Towson, J. C. J. Org. Chem. 1986, 51, 2402. Abstract
  3. ^  An Electrochemical Approach to the Guanacastepenes Chambers C. Hughes, Aubry K. Miller, and Dirk Trauner ORGANIC LETTERS 2005 Vol. 7, No. 16 3425-3428 Article
 
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.
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