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A Comparison of Two Effective Chiral Auxiliaries - (2R)-bornane-10,2-sultam and (2R)-bornane-10,2-cyclohydrazide - using the [4+2] Cycloaddition of Cyclopentadiene to their N,N'-fumaroyl derivatives
* 1 , 2 , 1, 2
1  Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, PL-01-224 Warsaw
2  Department of Chemistry, University of Warsaw, Pasteura 1, PL-02-093 Warsaw

Abstract: A correlation between the solvent polarity and the logarithm of the diastereoisomer ratio (dr) was found for the uncatalyzed [4+2] cycloaddition of cyclopentadiene to N,N'-fumaroyldi[(2R)-bornane-10,2-(2'phenyl-pyrazol-3'-one)]. Using the Abboud-Abraham-Kamlet-Taft parameters, predictive values for this method, allowed an optimum diastereoisomeric excess (de) of 94% in CHCl3. Implications for the stereochemical course of the reaction as well as a comparison with the (2R)-bornane-10,2-sultam analogous auxiliary are discussed.
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