1.
Org Lett
; 16(3): 727-9, 2014 Feb 07.
Article
in English
| MEDLINE
| ID: mdl-24446807
ABSTRACT
Redox transformation of an α,ß-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.
Subject(s)
Aldehydes/chemistry , Carboxylic Acids/chemical synthesis , Cyanides/chemistry , Trimethylsilyl Compounds/chemistry , Carboxylic Acids/chemistry , Kinetics , Molecular Structure , Oxidation-Reduction , Stereoisomerism , Thermodynamics
2.
