Alkyl 4,5-dihydrofuran-2-carboxylates can be efficiently obtained via an enantioselective organocatalyzed consecutive reaction between α-keto esters and (<i>Z</i>)-(2-chloro-2-nitroethenyl)benzenes. The overall sequence combines a (<i>R</i>,<i>R</i>)-TUC-catalyzed Michael addition with a DABCO-promoted intramolecular <i>O</i>-alkylation leading to the title products as single diastereomers with enantiomeric excesses from 86% up to 97%.