Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines

✍ Scribed by Kyohei Tokioka; Satoshi Masuda; Tomomi Fujii; Yasuo Hata; Yukio Yamamoto

• Book ID: 104360931
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 425 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(96)00473-9

✦ Synopsis

Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral Nsubstituted 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.