6533b7dbfe1ef96bd1270017

RESEARCH PRODUCT

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

Amparo Sanz-marcoGonzalo BlayJosé R. PedroCarlos VilaM. Carmen MuñozAdrián Laviós

subject

Cycloaddition ReactionCatàlisiCompostos orgànicsOrganic ChemistryEstersStereoisomerismPhysical and Theoretical ChemistryBiochemistryCatalysisBenzofuransReaccions químiques

description

The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans and α-aryl-α-isocyanoacetate esters provides tricyclic compounds bearing the 3a,8b-dihydro-1H-benzofuro[2,3-c]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.

yearjournalcountryeditionlanguage
2022-01-01
10.1021/acs.orglett.2c00427https://doi.org/10.1021/acs.orglett.2c00427