Double cascade reactions based on the Barbas dienamine platform: highly stereoselective synthesis of functionalized cyclohexanes for cardiovascular agents.
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.
Ramachary
Dhevalapally B
DB
School of Chemistry, University of Hyderabad, Hyderabad-500 046, India. ramsc@uohyd.ernet.in
Reddy
Y Vijayendar
YV
Prakash
B Veda
BV
D000596:Amino Acids / Q000737:chemistry; D002317:Cardiovascular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013379:Substrate Specificity
D000596:Amino Acids; D002317:Cardiovascular Agents; D003510:Cyclohexanes