Remote Functionalization of 4-(Alk-1-en-1-yl)-3-Cyanocoumarins via the Asymmetric Organocatalytic 1,6-Addition.

An organocatalytic 1,6-addition using 4-(alk-1-en-1-yl)-3-cyanocoumarins as acceptors has been developed. Dienolates derived from 5-substituted-furan-2(3H)-ones have been employed as pronucleophiles, therefore, enabling the synthesis of hybrid molecules bearing two biologically relevant units. Appropriate design of substrates and the application of quinine-derived catalyst resulted in very good site-selectivity as well as chemical and stereochemical efficiency of the process. [ABSTRACT FROM AUTHOR]