Polyethylene glycol (PEG) as a reusable solvent medium for an asymmetric organocatalytic Michael addition. Application to the synthesis of bioactive compounds

Author(s)

Feu, Karla S. ^[1] ; de la Torre, Alexander F. ^[1] ; Silva, Sandrina ^[1] ; de Moraes Junior, Marco A. F. ^[1] ; Correa, Arlene G. ^[1] ; Paixao, Marcio W. ^[1]

Affiliation

^[1] Univ Fed Sao Carlos, Dept Chem, BR-13560 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: GREEN CHEMISTRY; v. 16, n. 6, p. 3169-3174, 2014.
• Web of Science Citations: 30

Abstract

A highly stereoselective organocatalytic Michael addition of aldehydes to trans-beta-nitrostyrenes using PEG as a recyclable solvent medium is presented. The scope of this organocatalytic system is demonstrated by the formation of several Michael adducts in good yields and stereoselectivities. Furthermore, applying this new protocol to acetaldehyde, we have disclosed an easy formal synthesis of (R)-pregabalin, (R)-phenibut and (R)-bacoflen with good yields and outstanding enantioselectivities. (AU)

• FAPESP's process: 12/04986-5 - Asymmetric Organocatalysis: Development of New Methodologies and Application in Total Synthesis
• Grantee: Sandrina Isabel Ribeiro Martins da Silva
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 09/07281-0 - Asymmetric organocatalysis: design of new organocatalysts and development of new methodologies
• Grantee: Márcio Weber Paixão
• Support Opportunities: Research Grants - Young Investigators Grants