1370516-45-2Relevant academic research and scientific papers
Synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by ru(η5-C5Ph5)(CO)2Cl
Bartoszewicz, Agnieszka,Jezowska, Martina M.,Laymand, Kevin,Moebus, Juri,Martin-Matute, Belen
, p. 1517 - 1530 (2012)
An efficient method for the synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by Ru(η5-C 5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of the catalyst on the reaction outcome has been studied. Optimization of the reaction conditions supressed the formation of undesired side products such as saturated ketones, benzyl alcohols, and α,β-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce β-hydroxy ketones or β-amino ketones, respectively, in yields up to 99a%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized. β-Hydroxy and β-amino ketones are synthesized from allylic alcohols and aldehydes or imines, respectively. The coupling reaction is catalyzed by Ru(η5-C5Ph5)(CO) 2Cl. Mechanistic investigations support a mechanism via ruthenium alkoxide intermediates.
