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DOI: 10.1055/s-0030-1259550
The First Organocatalysed Direct Aldol Reaction of 2-Hydroxycyclobutanone
Publication History
Publication Date:
11 February 2011 (online)

Abstract
l-Tryptophan has been shown to catalyse the enantioselective aldol reaction between 2-hydroxycyclobutanone and an aromatic aldehyde in DMF solution. The reaction is completely regioselective and gives the 2,2-disubstituted cyclobutanone in up to 80% yield. The major adduct is obtained with ee values up to 67%, and has an anti relative configuration which contrasts with the selectivity of organocatalysed aldol reactions conducted on acyclic hydroxyacetone substrates.
Key words
cyclobutanone - tryptophan - organocatalysis - aldol reaction - stereoselective reaction.
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References
Very recently it was reported that l-Trp did not catalyse the aldol reaction of hydroxyacetone with 4 in water, see ref. 16a.
18CCDC 772896 contains the supplementary crystallographic data for anti-4. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.