188401-87-8Relevant academic research and scientific papers
Asymmetric cycloaddition of anthrone with n-substituted maleimides with C2-chiral pyrrolidines
Tokioka, Kyohei,Masuda, Satoshi,Fujii, Tomomi,Hata, Yasuo,Yamamoto, Yukio
, p. 101 - 107 (2007/10/03)
Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration Of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de.
