Synthesis of β-Hydroxy and β-Amino Ketones from Allylic Alcohols Catalyzed by Ru(η5-C5Ph5)(CO)2Cl
2012 (English)In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-0682, no 9, 1517-1530 p.Article in journal (Refereed) Published
An efficient method for the synthesis of beta-hydroxy and beta-amino ketones from allylic alcohols catalyzed by Ru(5-C5Ph5)(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 a,beta-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce beta-hydroxy ketones or beta-amino ketones, respectively, in yields up to 99%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized.
Place, publisher, year, edition, pages
2012. no 9, 1517-1530 p.
Synthetic methods, Homogeneous catalysis, Ruthenium, Isomeri-zation, Allylic alcohols, Amines, Mannich reaction, Aldols, Ketones
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-76270DOI: 10.1002/ejic.201101014ISI: 000301494500028OAI: oai:DiVA.org:su-76270DiVA: diva2:527409
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation