EventsThe 4th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-4-01817
This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry
Published date
11 Sep, 2000
Citation
Janusz Jurczak, Anna Kucharska, Christian Chapuis, 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, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, 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
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.
Keywords
n/a
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