TMSCN/DBU-mediated facile redox transformation of α,β-unsaturated aldehydes to carboxylic acid derivatives.
Redox transformation of an α,β-unsaturated aldehyde to a carboxylic acid derivative by means of a combination of TMSCN and DBU was investigated. In addition to the wide use of the carboxylic acid derivatives provided by this reaction, temperature-dependent control of the kinetic or thermodynamic protonation pattern was found to selectively switch the stereochemistry of the acyl group in the product.
Graduate School of Pharmaceutical Sciences, University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Hiromi
H
Kaise
Jun
J
Shimokawa
Tohru
T
Fukuyama
D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013816:Thermodynamics; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000447:Aldehydes; D002264:Carboxylic Acids; D003486:Cyanides; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide