19804-64-9Relevant articles and documents
Iron-catalyzed carbonylation-peroxidation of alkenes with aldehydes and hydroperoxides
Liu, Weiping,Li, Yuanming,Liu, Kaisheng,Li, Zhiping
, p. 10756 - 10759 (2011/08/22)
A three-component reaction of alkenes, aldehydes, and hydroperoxides catalyzed by FeCl2 to β-peroxy ketones has been achieved. This three-component reaction can be also applied to the synthesis of α-carbonyl epoxides, through either a stepwise base-induced epoxidation of the separated β-peroxy ketone products or a one-pot process by simply adding base to the reaction mixture after the completion of the three-component reaction.
Synthesis, Structure, and Sterreoselective Reaction of a Chiral Hydroxy-Stabilized Metal-Free Enolate
Reetz, Manfred T.,Huette, Stephan,Goddard, Richard,Robyr, Chantal
, p. 382 - 384 (2007/10/03)
The reaction of acetophenone with tetrabutylammonium hydroxide affords the tetrabutylammonium enolate of phenyl (2-hydroxy-2-phenyl)propyl ketone.The crystal structure of this chiral enolate shows intramolecular hydrogen bonding between the hydroxyl group and the enolate oxygen atom.Furthermore, the α-methylene units of the ammonium counterion form hydrogen bonds to the basic enolate C and O atoms and to the O atom of the hydroxy group.This three-point bonding occurs selectively on the Re,Re side, a phenomenon which may be responsible for the direction of diastereoselectively in the epoxide-forming reaction of the enolate with N-bromosuccinimide. - Keywords: asymmetric synthesis; chirality; enolates; hydrogen bonds; structure elucidation