A defunctionalization concept for the convenient synthesis of bis(5-arylfuran-2-yl)methane scaffolds

Article abstract of DOI:10.1002/ejoc.201301319

The bis(5-arylfuran-2-yl)methane framework has been obtained through defunctionalization of aryl ketones, derived from abundantly available L-(+)-tartaric acid, under the influence of acid. The stereocomponents present in these starting aryl ketones have been found to be insignificant for this transformation. Formation of bis(5-arylfuran-2-yl)methane scaffold 1 has been achieved by using a defunctionalization concept involving aryl ketones 2 under the influence of acid. Ketones 2 are easily accessible from L-(+)-tartaric acid through an umpolung strategy using α-amino nitriles as acyl anion equivalents. The stereocomponent (threo/erythro) present in 2 was not significant for this transformation. Copyright