Double cascade reactions based on the Barbas dienamine platform: highly stereoselective synthesis of functionalized cyclohexanes for cardiovascular agents

Ramachary, Dhevalapally B. ; Reddy, Y. Vijayendar ; Prakash, B. Veda (2008) Double cascade reactions based on the Barbas dienamine platform: highly stereoselective synthesis of functionalized cyclohexanes for cardiovascular agents Organic and Biomolecular Chemistry, 6 (4). p. 719. ISSN 1477-0520

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Official URL: http://doi.org/10.1039/B718122A

Related URL: http://dx.doi.org/10.1039/B718122A

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to The Royal Society of Chemistry.
ID Code:120773
Deposited On:05 Jul 2021 06:33
Last Modified:05 Jul 2021 06:33

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