Synthesis of β-Hydroxy and β-Amino Ketones from Allylic Alcohols Catalyzed by Ru(η5-C5Ph5)(CO)2Cl

• 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.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

Synthetic methods

Homogeneous catalysis

Ruthenium

Isomeri-zation

Allylic alcohols

Amines

Mannich reaction

Aldols

Ketones

organisk kemi

Organic Chemistry

Publikations- och innehållstyp

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