One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction to access 5-quaternary-4-amidocyclopent-2-enones and 2-quaternary-3-amidoindanones

Abstract

A one-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction has been explored for the first time, facilitating the synthesis of the unprecedented 2,3-disubstituted-5-quaternary-4-amidocyclopent-2-enone and 2-quaternary-3-amidoindanones. This transformation features convenient operation, good yields (up to 70%), and good to excellent diastereoselectivity (up to 20 : 1). The proposed reaction mechanism is supported by some experimental results.