2-Amino-3-cyanochromene is a privileged scaffold and it can be found in pharmacological agents as the antitumor Crolibulin and the pro-apoptotic HA14-1. Recent studies have also shown that chromene phosphonyl derivatives exhibit different biological activities including antifungal, antimicrobial, antioxidant and anticancer ones. Since it is known that each enantiomer could present distinct biological properties, the development of an asymmetric catalytic procedure to obtain these enantioenriched products is still desirable. Following this idea, the present research explores the use of chiral organocatalysts in several reactions for the synthesis of these interesting derivatives. To date, preliminary results obtained following two organocatalytic strategies using diarylphosphonates (Pudovik reaction) and trialkylphosphites (Abramov reaction) showed an adequate chiral induction, providing the first examples of enantioselective synthesis of chromene phosphonyl derivatives.
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First Advances in the Asymmetric Synthesis of Biologically Active 2-Amino-3-cyano-4H-chromen-4yl Phosphonates
Published: 01 November 2017 by MDPI in 3rd International Electronic Conference on Medicinal Chemistry session Posters
Keywords: organocatalysis, asymmetric organocatalysis, chromene, privileged scaffold