Journal
ORGANIC LETTERS
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02836
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- National Science Centre, Poland [UMO-2015/18/E/ST5/00309]
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A novel organocatalytic reaction cascade has been described for the stereocontrolled functionalization of cyanocoumarins, producing biologically active coumarin and delta-lactone-fused products.
A novel organocatalytic reaction cascade between 3-cyano-4-styrylcoumarins and 2-mercaptoacetophenones is described. It is based on stereocontrolled functionalization of cyanocoumarins proceeding in a sequence of thia-Michael/aldol/annulation reactions. This highly diastereo- and enantioselective reaction is realized by employing enantioselective bifunctional catalysis and exhibits a broad substrate scope and excellent functional group tolerance. The synthetic application involves the transformation of the imidoester group, thus opening access to biologically relevant coumarin and delta-lactone-fused products.
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