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Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters

Adrián Laviós, Amparo Sanz‐Marco, Carlos Vila, M. Carmen Muñoz, José R. Pedro, Gonzalo Blay

2022Organic Letters15 citationsDOIOpen Access PDF

Abstract

]pyrrole framework with three consecutive stereogenic centers. The reaction was enabled by a cupreine-ether organocatalyst. The reaction products were obtained with almost full diastereoselectivity and with excellent enantiomeric excesses for a number of substituted 2-nitrobenzofurans and isocyanoacetates.

Topics & Concepts

StereocenterChemistryEnantioselective synthesisCycloadditionFormal synthesisPyrroleEnantiomerArylEtherStereochemistryOrganic chemistryCatalysisAlkylAsymmetric Synthesis and CatalysisOxidative Organic Chemistry ReactionsCyclopropane Reaction Mechanisms