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Synthesis 1993; 1993(5): 475-477
DOI: 10.1055/s-1993-25885
short paper
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A Practical Synthesis of (R)-(+)-Cyclohex-3-enecarboxylic Acid via an Asymmetric Diels-Alder Reaction

Catriona Thom* , Philip Kocieński, Krzysztof Jarowicki
  • *Department of Chemistry, The University, Southampton, SO9 5NH, England
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Publication Date:
17 September 2002 (online)

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The polymerisation which complicates the ethylaluminum dichloride-catalysed asymmetric Diels-Alder reaction between N-propenoylbornane-10,2-sultam [10,10-dimethyl-3-thia-4-azatricyclo-[5.2.1.01,5]decane 3,3-dioxide] and butadiene can be suppressed using galvinoxyl [2,6-di-tert-butyl-α-(3, 5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-tolyloxyl] leading to a practical and large scale synthesis of (R)-(+)-cyclohex-3-enecarboxylic acid.