189291-16-5Relevant academic research and scientific papers
Regiospecific ring-opening reactions of β-aziridinyl ct, β-enoates with acids: Application to the stereoselective synthesis of a couple of diastereoisomeric (Zi)-alkene dipeptide isosteres from a single β-aziridinyl a, β-enoate and to the convenient preparation of amino alcohols bearing a, β-unsaturated ester groups
Tamamura, Hirokazu,Yamashita, Masaki,Nakajima, Yutaka,Sakano, Kyoko,Otaka, Akira,Ohno, Hiroaki,Ibuka, Toshiro,Fujii, Nobutaka
, p. 2983 - 2996 (2007/10/03)
Regio- and stereo-selective ring-opening reactions of N-(2, 4, 6-trimethylphenylsulfonyl)-γ, δ-cis- or trans-γ, δ-epimino (E)-α, β-enoates with acids such as methanesulfonic acid (MSA) or trifluoroacetic acid (TFA) have been found. These ring-opening reactions are useful for the stereoselective synthesis of a couple of diastereomeric (￡)-alkene dipeptide isosteres from a single substrate of γ, δ-epimino (E)-α, β-enoate, and for the convenient preparation of δ-aminated γ-hydroxy α, β-enoates. The Royal Society of Chemistry 1999.
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 (2007/10/03)
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.
A thermodynamic preference of chiral cis-γ,δ-epimino-(E)-α,β-unsaturated esters over other stereoisomers: Synthetically useful Pd(0)-catalyzed equilibrated reactions of aziridines bearing an α,β-unsaturated ester group
Ibuka, Toshiro,Akaji, Masako,Mimura, Norio,Habashita, Hiromu,Nakai, Kazuo,Tamamura, Hirokazu,Fujii, Nobutaka,Yamamoto, Yoshinori
, p. 2849 - 2852 (2007/10/03)
A practical synthesis of chiral N-arylsulfonyl-cis-γ,δ-epimino-(E)-α,β-enoates, key intermediates for the synthesis of (E)-alkene dipeptide isosteres via Pd(0)-catalyzed equilibrated reactions, has been successfully achieved by exposing N-arylsulfonyl-γ,δ
