title: Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an alpha,beta-Unsaturated Ester Group: A Thermodynamic Preference for Chiral Alkyl (2E)-4,5-cis-4,5-Epimino-N-(alkyl- or arylsulfonyl) 2-Enoates over the Other Three Stereoisomers.
abstract: 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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980, Japan.
authors.forename: Toshiro
authors.initials: T
authors.lastname: Ibuka
authors.forename: Norio
authors.initials: N
authors.lastname: Mimura
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
authors.forename: Kazuo
authors.initials: K
authors.lastname: Nakai
authors.forename: Masako
authors.initials: M
authors.lastname: Akaji
authors.forename: Hiromu
authors.initials: H
authors.lastname: Habashita
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Tamamura
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Miwa
authors.forename: Tooru
authors.initials: T
authors.lastname: Taga
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Yamamoto