201487-15-2Relevant 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 (1999)
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.
Regiospecific ring-opening reactions of aziridines bearing an α,β-unsaturated ester group with trifluoroacetic acid or methanesulfonic acid: Application to the stereoselective synthesis of (E)-alkene dipeptide isosteres
Tamamura, Hirokazu,Yamashita, Masaki,Muramatsu, Hiroyuki,Ohno, Hiroaki,Ibuka, Toshiro,Otaka, Akira,Fujii, Nobutaka
, p. 2327 - 2328 (2007/10/03)
Reaction of N-(2,4,6-trimethylphenylsulfonyl)-γ,δ-cis- or -trans-γ,δ-epimino (E)-α,β-enoates with acids such as TFA or methanesulfonic acid (MSA) affords the stereo- and regio-selective ring-opened products in high yields, and subsequent treatment of resulting δ-aminated γ-mesyloxy α,β-enoates with organocopper reagents yields diastereoisomerically pure (E)-alkene dipeptide isosteres.
