Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 4, Pages 719-726Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b718122a
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The amino acid proline catalyzed the three- and five-component cascade olefination-Diels-Alder -epimerization and olefination -Diels-Alder-epimerization-olefination-hydrogenation reactions of readily available precursors enones 1a-i, arylaldehydes 2a-k, alkyl cyanoacetates 3a-e and Hantzsch ester 9 to furnish highly substituted prochiral 1-cyano-4-oxo-2,6-diaryl-cyclohexanecarboxylic acid alkyl esters 6 and 1-cyano-4-(cyano-alkoxycarbonyl-methyl)-2,6-diaryl-cyclohexanecarboxylic acid alkyl esters 10 in a highly diastereoselective fashion with excellent yields. Prochiral cis-isomers 6 are excellent starting materials for the synthesis of cardiovascular agents and hypnotic active products.
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