Polymergebundene Cinchonaalkaloide als Katalysatoren in der Michael Reaktion

✍ Scribed by Kurt Hermann; Hans Wynberg

• Publisher: John Wiley and Sons
• Year: 1977
• Tongue: German
• Weight: 294 KB
• Volume: 60
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19770600713

✦ Synopsis

Polymer Bound Cinchona Alkaloids as Catalysts in the Michael Reaction

Three insoluble chiral polymers (6, 7 and 8) were prepared by functionalization of copoly(styrene −2% divinyl benzene) followed by reaction with quinine (9) or dihydrocupreine (10). Their utility as catalysts in the reaction between methyl indane‐1‐one‐2‐carboxylate (13) and 3‐butene‐2‐one (14) was studied. Table 1 (runs 2–6 and 8) shows that the Michael‐adduct 15 was formed in good chemical but low optical yields, independent of the chiral polymer used. These results are compared with those of the Michael reactions in the presence of the monomeric bases quinine (9), O‐acetyl‐quinine (11) and eucipine (12) (runs 1, 7 and 9).