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Polymergebundene Cinchonaalkaloide als Katalysatoren in der Michael Reaktion
Author(s) -
Hermann Kurt,
Wynberg Hans
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600713
Subject(s) - chemistry , michael reaction , adduct , polymer chemistry , catalysis , cinchona alkaloids , benzene , styrene , polymer , organic chemistry , quinine , monomer , indane , medicinal chemistry , copolymer , enantioselective synthesis , malaria , immunology , biology
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).