73522-75-5Relevant academic research and scientific papers
Expansion of the aromatic part of Cinchona alkaloids. Annulation of quinolines with phenoxazine motifs
W?sińska-Ka?wa, Ma?gorzata,Giurg, Miros?aw,Boratyński, Przemys?aw J.,Skar?ewski, Jacek
, p. 308 - 315 (2017/12/08)
An oxidative cross-coupling strategy for quinoline ring annulation in Cinchona alkaloids has been developed. Key-reaction optimization by changing oxidants and adjusting the nucleophilicity of the 2-aminophenols led to cupreine and cupreidine expanded with the phenoxazinone unit in 56–75% yield. The stereochemical integrity of the obtained alkaloid structures was confirmed by combined experimental and computed CD and NMR data. The conformational study revealed a fast equilibrium of the three conformers, differing in the orientation of the pyrido[a-3,2]phenoxazine moiety.
β-Isocupreidine-hexafluoroisopropyl acrylate method for asymmetric Baylis-Hillman reactions
Nakano, Ayako,Kawahara, Sakie,Akamatsu, Saori,Morokuma, Kenji,Nakatani, Mari,Iwabuchi, Yoshiharu,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
, p. 381 - 389 (2007/10/03)
Key features of the β-isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reaction of aldehydes with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) are presented. In addition, an improved method using azeotropically dried β-ICD is described.
