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 arylsulfonyl) 2-Enoates over the Other Three Stereoisomers
The Journal of Organic Chemistry1997Vol. 62(9), pp. 2982–2991
Citations Over TimeTop 10% of 1997 papers
Toshiro Ibuka, Norio Mimura, Hiroaki Ohno, Kazuo Nakai, Masako Akaji, Hiromu Habashita, Hirokazu Tamamura, Yoshihisa Miwa, Tooru Taga, Nobutaka Fujii, Yoshinori Yamamoto
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.
Related Papers
- → Efficient Approach to Medium-sized Cyclic Molecules Containing (E)-Alkene via Z to E Photochemical Isomerization in the Presence of AgNO3-impregnated Silica Gel(2018)8 cited
- → Surface-assisted cis–trans isomerization of an alkene molecule on Cu(110)(2013)12 cited
- → Highly Stereoselective Isomerization of Monosubstituted 1-Alkenes to (E)-2-Alkenes by Catalysis of (C5Me5)2TiCl2/NaC10H8(1983)73 cited
- → Evidence for Ruthenium(II) Peralkene Complexes as Catalytic Species during the Isomerization of Terminal Alkenes in Solution(2023)2 cited
- → Isomerization and Hydrogenation of Alkenes(2017)2 cited