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Dendritic Amplification of Stereoselectivity of a Prolinamide‐Catalyzed Direct Aldol Reaction
Author(s) -
Mitsui Kazuhiko,
Parquette Jon R.
Publication year - 2009
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1560/ijc.49.1.119
Subject(s) - chemistry , dendrimer , stereoselectivity , aldol reaction , aldol condensation , catalysis , monomer , enantioselective synthesis , organocatalysis , combinatorial chemistry , organic chemistry , polymer
Isomeric “ compact ” and “expanded” dendrimers functionalized with L ‐prolinamide catalytic units at the periphery were compared as catalysts to monomer controls in the organocatalytic direct aldol condensation. A positive dendritic effect that amplifies the stereoselectivity of the direct aldol condensation was observed for dendrimers 3 and 4 , compared with lower molecular weight catalysts L ‐prolinani‐lide 1 and G1 dendron 2 . The difference in the compactness between 3 and 4 appears to have less impact on the stereoselectivity than the preorganized multivalency of the dendritic catalysts.