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; Anna Kucharska; Janusz Jurczak

doi:10.3390/ecsoc-4-01817

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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

Christian Chapuis

^{*

1},

Anna Kucharska

²,

Janusz Jurczak

^{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

Published: 11 September 2000 by MDPI in The 4th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

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

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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Christian Chapuis

Anna Kucharska

Janusz Jurczak