We report highly enantioselective examples of the Rauhut−Currier cycloisomerization reaction (the “vinylogous Morita−Baylis−Hillman reaction”). The reaction is highly practical and is catalyzed by a commercially available derivative of the proteinogenic amino acid cysteine. Reactions are conducted in the presence of potassium tert -butoxide and a critical concentration of water in bulk acetonitrile. A mechanistic model is advanced that may account for reaction selectivity that is predicated on organizational chelation of K ion in the product-determining step in which the Cys derivative undergoes elimination.
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Aroyan et al. (2006) studied this question.
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