Categories: C-C Bond Formation > Oxygen-containing molecules >

Synthesis of α-keto carboxylic acids, esters and amides

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Recent Literature

A tandem three-step, one-pot method for the conversion of aldehydes into β-substituted-2-oxohex-5-enoic acids in good to excellent yield is described. The optimised sequence is carried out in water with microwave irradiation and involves sequential Horner-Wadsworth-Emmons (HWE) olefination, Claisen rearrangement and ester hydrolysis. The outcome of this domino sequence can be controlled by the temperature of the process.
E. Quesada, R. J. K. Taylor, Synthesis, 2005, 3193-3195.

While 3,4;5,6-di-O-isopropylidene-N-phthaloyl-D-glucosamine propane-1,3-diyl dithioacetal underwent fast β-elimination, the corresponding N-acetyl derivative was easily deprotonated with butyllithium to form the dilithiated intermediate. Stoichiometry and temperature were crucial factors for selective C-C coupling with various electrophiles.
Y.-L. Chen, R. Leguijt, H. Redlich, R. Fröhlich, Synthesis, 2006, 4212-4218.