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Synthesis of β‐Hydroxy and β‐Amino Ketones from Allylic Alcohols Catalyzed by Ru(η 5 ‐C 5 Ph 5 )(CO) 2 Cl
Author(s) -
Bartoszewicz Agnieszka,
Jeżowska Martina M.,
Laymand Kévin,
Möbus Juri,
MartínMatute Belén
Publication year - 2012
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201101014
Subject(s) - chemistry , ruthenium , allylic rearrangement , catalysis , ketone , organic chemistry , medicinal chemistry
An efficient method for the synthesis of β‐hydroxy and β‐amino ketones from allylic alcohols catalyzed by Ru(η 5 ‐C 5 Ph 5 )(CO) 2 Cl 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 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.