493006-79-4Relevant academic research and scientific papers
Practical synthesis of chiral emopamil left hand as a bioactive motif.
Kimura, Teiji,Yamamoto, Noboru,Suzuki, Yuichi,Kawano, Koki,Norimine, Yoshihiko,Ito, Koichi,Nagato, Satoshi,Iimura, Yoichi,Yonaga, Masahiro
, p. 6228 - 6231 (2007/10/03)
An asymmetric synthesis of (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile (emopamil left hand, 2) has been completed by use of the MAD (methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide)-induced rearrangement of a chiral epoxyalcohol as the key reaction. The stereochemistry of the chiral quaternary center was confirmed by transformation of 2 to (S)-noremopamil. This method requires minimal purification procedures and affords high chemical and optical yields. Acid-catalyzed isomerization of an allylaldehyde and retro-aldol type racemization at the quaternary carbon of a nitrile-alcohol were encountered.
Enantioselective synthesis of (2S)-5-{4-[2-(4-fluorophenoxy)ethyl]piperazin-1-yl}-2-isopropyl-2-phenyl- pentanenitrile dihydrochloride (E2050) using enzyme-catalyzed kinetic resolution
Norimine, Yoshihiko,Yamamoto, Noboru,Suzuki, Yuichi,Kimura, Teiji,Kawano, Koki,Ito, Koichi,Nagato, Satoshi,Iimura, Yoichi,Yonaga, Masahiro
, p. 1493 - 1502 (2007/10/03)
Immobilized lipase (Pseudomonas sp.)-catalyzed transesterification of (RS)-4-cyano-4-isopropyl-4-phenyl-1-butanol 4 in vinyl acetate gave (S)-4-cyano-4-isopropyl-4-phenyl-1-butyl acetate 3a with high enantiomeric excess values and conversions (95-97% ee,
