Enantioselective Synthesis of α-Allyl-α-aryldihydrocoumarins and 3-Isochromanones via Pd-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

• DOI: 10.1021/acs.orglett.6b02584
• Publication Date: 2016-10-26T05:01:07Z
• Authors: Ramulu Akula; Patrick J. Guiry
• Keywords: Tsuji–Trost reaction

An enantioselective Pd-catalyzed DAAA of α-aryl-β-oxo esters has been developed employing the (R,R)-ANDEN-phenyl Trost ligand to prepare a series α-aryl-α-allyldihydrocoumarins and 3-isochromanones. A variety aryl groups were successfully employed afford dihydrocoumarin 3-isochromanone products in high yields up 95% ee's 96%. Under these conditions, substrates containing di- mono-ortho-substituted gave highest levels enantioselectivities. This work represents first example preparation all-carbon quaternary α-allyl-α-aryl dihydrocoumarins