189291-10-9Relevant academic research and scientific papers
Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an α,β-Unsaturated Ester Group: A Thermodynamic Preference for Chiral Alkyl (2E)-4,5-cis-4,5-Epimino-N-(alkyl- or arylsvdfonyl) 2-Enoates over the Other Three Stereoisomers
Ibuka, Toshiro,Mimura, Norio,Ohno, Hiroaki,Nakai, Kazuo,Akaji, Masako,Habashita, Hiromu,Tamamura, Hirokazu,Miwa, Yoshihisa,Taga, Tooru,Fujii, Nobutaka,Yamamoto, Yoshinori
, p. 2982 - 2991 (1997)
Palladium(0)-catalyzed reactions of five sets of four stereoisomeric 4,5-epimino-N-(methanesulfonyl) or -N-(arylsulfonyl) 2-enoates reveal that 4,5-cis-(2E)-isomers are thermodynamically more stable than other isomers, in accord with calculations. A highly stereoselective synthesis of (E)-alkene dipeptide isosteres having the desired stereochemistries from unwanted stereoisomeric 4,5-epimino-N-(arylsulfonyl) 2-enoates is also presented.
