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Issue 4, 2008
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Double cascade reactions based on the Barbas dienamine platform: highly stereoselective synthesis of functionalized cyclohexanes for cardiovascular agents

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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.

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

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Article information


Submitted
23 Nov 2007
Accepted
29 Nov 2007
First published
09 Jan 2008

Org. Biomol. Chem., 2008,6, 719-726
Article type
Paper

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

D. B. Ramachary, Y. V. Reddy and B. V. Prakash, Org. Biomol. Chem., 2008, 6, 719
DOI: 10.1039/B718122A

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