Asymmetric Synthesis of Tetrahydrobenzofurans and Annulated Dihydropyrans via Cooperative One-Pot Organo- and Silver-Catalysis

In memory of Professor Jean Normant

Abstract

A low catalyst loading of a squaramide (0.5 mol%) and a silver(I) salt (1 mol%) efficiently catalyzes a one-pot asymmetric Michael addition/hydroalkoxylation reaction between 1,3-diketones and alkyne-tethered nitroalkenes. Depending on the 1,3-dicarbonyl substrate this cooperative catalytic approach opens access to tetrahydrobenzofurans or annulated dihydropyrans in moderate to excellent yields and very good to excellent enantioselectivities.

Key words

asymmetric synthesis - organocatalysis - one-pot synthesis - silver catalysis - annulation

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