TY - JOUR
T1 - One-pot multi-component asymmetric cascade reactions catalyzed by soluble star polymers with highly branched non-interpenetrating catalytic cores
AU - Chi, Yonggui
AU - Scroggins, Steven T.
AU - Fréchet, Jean M.J.
PY - 2008/5/21
Y1 - 2008/5/21
N2 - Non-interpenetrating star polymer catalysts designed to mimic the site isolation characteristics of enzymes enable the one-pot combination of multiple otherwise incompatible catalysts for asymmetric cascade reactions that involve iminium, enamine, and H-bonding catalysis. Control experiments replacing star polymer catalysts with the corresponding small molecule or linear polymer analogues lead to little or no cascade reaction. Our strategy also allows straightforward access to all possible stereoisomers of the cascade product individually by proper choice of catalyst chirality. To our knowledge, this work represents the most sophisticated study of soluble polymers for site isolation, enzyme-like catalysis that generates cascade products with multiple chiral centers.
AB - Non-interpenetrating star polymer catalysts designed to mimic the site isolation characteristics of enzymes enable the one-pot combination of multiple otherwise incompatible catalysts for asymmetric cascade reactions that involve iminium, enamine, and H-bonding catalysis. Control experiments replacing star polymer catalysts with the corresponding small molecule or linear polymer analogues lead to little or no cascade reaction. Our strategy also allows straightforward access to all possible stereoisomers of the cascade product individually by proper choice of catalyst chirality. To our knowledge, this work represents the most sophisticated study of soluble polymers for site isolation, enzyme-like catalysis that generates cascade products with multiple chiral centers.
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U2 - 10.1021/ja8013456
DO - 10.1021/ja8013456
M3 - Article
C2 - 18433122
AN - SCOPUS:43949131082
SN - 0002-7863
VL - 130
SP - 6322
EP - 6323
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 20
ER -