Structural effects in pyrazolidinone-mediated organocatalytic Diels–Alder reactions

E Gould, T Lebl, AMZ Slawin, M Reid, AD Smith

Index: Gould, Eoin; Lebl, Tomas; Slawin, Alexandra M.Z.; Reid, Mark; Smith, Andrew D. Tetrahedron, 2010 , vol. 66, # 46 p. 8992 - 9008

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Citation Number: 21

Abstract

A range of pyrazolidin-3-ones have been prepared and their activity as catalysts for iminium- ion promoted Diels–Alder reactions evaluated. Systematic variation of the C (5)-and N (2)- substituents indicates that the incorporation of an electron withdrawing substitutent at N (2) and either a Ph or CF3 substitution at C (5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C (5)-Ph substituted pyrazolidinone and its ability ...