Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Supported and Unsupported Chiral Squaramides as Organocatalysts for Stereoselective Michael Additions: Synthesis of Enantiopure Chromenes and Spirochromanes

Supported and Unsupported Chiral Squaramides as Organocatalysts for Stereoselective Michael Additions: Synthesis of Enantiopure Chromenes and Spirochromanes
José M. Andrés, Alicia Maestro, Jorge Losada, Rafael Pedrosa, Patricia Rodríguez-Ferrer
Novel supported chiral bifunctional squaramides have been easily prepared starting from diamines derived from natural amino acids and commercially available aminoalkyl polystyrene resins. These squaramides behave as excellent stereoselective recoverable organocatalysts in different Michael additions, in neat conditions at room temperature. The reaction on 2-(2-nitrovinyl) phenol as electrophile lead, in excellent yields and enantioselectivities, to intermediates that can be easily transformed into 4H-chromenes, and spirochromanones.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01177

DOI: 10.1021/acs.joc.7b01177

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