Journal
TETRAHEDRON
Volume 66, Issue 46, Pages 8992-9008Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.09.021
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- Royal Society
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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 to impart modest levels of asymmetric induction in the organocatalytic Diels-Alder reaction is also demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.
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