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

Christian Chapuis,Janusz Jurczak,Anna Kucharská

doi:10.3390/ecsoc-4-01817

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

Christian Chapuis, Janusz Jurczak + Show 1 more

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https://doi.org/10.3390/ecsoc-4-01817

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Publication Date: Sep 11, 2000

License type: cc-by

Affiliation: Polish Academy of Sciences, University of Warsaw

#Effective Chiral Auxiliaries #Stereochemical Course + Show 5 more

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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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