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Chemical Compound Review

Acyloin     3-hydroxyoctadecan-2-one

Synonyms: AG-J-98843, AC1Q5CBE, CTK5A6838, AR-1E4490, AR-1E4491, ...
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Disease relevance of Acyloin

  • [reaction: see text] Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage [1].

High impact information on Acyloin

  • The preparation of the corresponding C.1-C.12 segment of amphidinolide Y relies on asymmetric hydrogenation of an alpha-ketoester, a diastereoselective boron aldol reaction, and a chelate-controlled addition of MeMgBr in combination with suitable oxidation state management for the elaboration of the tertiary acyloin motif [2].
  • Carbene-catalyzed acyloin condensation of beta-aldehyde 10 followed by acetylation provided a separable mixture of diastereomeric (2S,5RS,7S)-diamino-4-oxo-5-acetoxysuberates (13) [3].
  • Minor side reactions involving the AR, the substrate acyloin, and the vinyl ester acyl donor were also observed [4].


  1. Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde. Demir, A.S., Seşenoglu, O., Dünkelmann, P., Müller, M. Org. Lett. (2003) [Pubmed]
  2. Total syntheses of amphidinolide X and Y. Fürstner, A., Kattnig, E., Lepage, O. J. Am. Chem. Soc. (2006) [Pubmed]
  3. Rigid dipeptide mimics: synthesis of enantiopure c6-functionalized pyrrolizidinone amino acids. Rao, M.H., Pinyol, E., Lubell, W.D. J. Org. Chem. (2007) [Pubmed]
  4. Chemoenzymatic dynamic kinetic resolution of acyloins. Odman, P., Wessjohann, L.A., Bornscheuer, U.T. J. Org. Chem. (2005) [Pubmed]
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