87712-80-9Relevant academic research and scientific papers
Novel asymmetric synthesis of atropisomeric 6-aryl pyrazinones via an unusual chirality transfer process
Tulinsky, John,Cheney, B. Vernon,Mizsak, Stephen A.,Watt, William,Han, Fusan,Dolak, Lester A.,Judge, Thomas,Gammill, Ronald B.
, p. 93 - 100 (2007/10/03)
Cyclization of (S,S)-α-[(1-phenylethyl)amino]-α-(2- iodophenyl)acetonitrile with (COCl)2 in toluene or chlorobenzene afforded the atropisomeric pyrazinone (aS,S) 6-(2-α-iodophenyl)-3,5-dichloro-1(1- phenylethyl)-2(1H)-pyrazinone in 57% yield. With smaller ortho substituents (F, Cl, CH3, CF'3, OCH3) on the aromatic ring, mixtures of atropisomers were obtained from the cyclization reaction. All of the individual atropisomers prepared were stable at room temperature. All but the o-fluoro- substituted atropisomers were stable at elevated temperatures. This paper describes a stereoselective synthesis of pyrazinones and suggests a mechanism for formation via an interesting transfer of chirality.
ASYMMETRIC SYNTHESIS OF α-AMINONITRILES
Mai, Khuong,Patil, Ghanshyam
, p. 1299 - 1304 (2007/10/02)
The asymmetric synthesis of α-aminonitriles was carried out by the reaction of α-trimethylsilyloxynitriles with optically active α-methylbenzylamine in methanol.The reactions provided moderate yields and good optical purities.
