24190-08-7Relevant academic research and scientific papers
A general synthesis of 2-alkoxy-2-phenylpropanoic acids
Monk, Keith A.,Duncan, Nathan C.,Bauch, Eric A.,Garner, Charles M.
, p. 8605 - 8609 (2008/12/21)
A preparation of a variety of 2-alkoxy-2-phenylpropanoic acids in two steps is described. Epoxidation of α-methylstyrene with mCPBA in methanol or primary alcohol solvents proceeded with an acid-catalyzed in situ ring opening reaction to give the corresponding 2-alkoxy-2-phenyl-1-propanols in 28-91% yield. Lower yields were realized with secondary (22-58%) and tertiary (14%) alcohols. These alcohols were cleanly oxidized to the corresponding carboxylic acids using a mild Heyns' oxidation (O2, Pt/C) in generally good to excellent yields (25-92%). The derived (S)-α-methylbenzylamide diastereomers are nearly all well separated by capillary GC, and the use of this method to determine the enantiomeric purity of brucine-resolved 2-methoxy-2-phenylpropanoic acid was demonstrated.
Asymmetric synthesis of both enantiomers of α-methyl-α-methoxyphenylacetic acid from l-(+)-tartaric acid: formal enantioselective synthesis of insect pheromone (-)-frontalin
Prasad, Kavirayani R.,Chandrakumar, Appayee,Anbarasan, Pazhamalai
, p. 1979 - 1984 (2007/10/03)
Both antipodes of α-methyl-α-methoxyarylacetic acid derivatives were prepared from a common chiralpool precursor l-(+)-tartaric acid. The key step involves the addition of Grignard reagents to 1,4-diketones derived from tartaric acid. The utility of this
Regioselective synthesis of optically active (pyrazolyl)pyridines with adjacent quaternary carbon stereocenter: Chiral N,N-donating ligands
Kowalczyk, Rafa?,Skarzewski, Jacek
, p. 623 - 628 (2007/10/03)
Novel optically active 2-(pyrazol-1-yl)pyridines have been prepared using resolved the O-methyl ether of atrolactic acid as a source of the adjacent quaternary carbon stereocenter. Different regioisomers were formed selectively in the reaction of 2-hydraz
Stereospecific Construction of Chiral Quaternary α-Oxygenated Aldehydes from Chiral Secondary Alcohol Derivatives
Arasaki, Hideki,Iwata, Masashi,Nishimura, Daisuke,Itoh, Akichika,Masaki, Yukio
, p. 546 - 548 (2007/10/03)
Chiral tertiary dichloromethylcarbinol derivatives 2, prepared from protected chiral secondary alcohols 1, were converted stereospecifically into chiral quaternary α-oxygenated aldehyde derivatives 4 and 11 via intermediary α-chloroepoxides 3 under weakly
