Enantioselective Organocatalyzed Consecutive Synthesis of Alkyl 4,5-Dihydrofuran-2-carboxylates from α-Keto Esters and (Z)-β-Chloro-β-nitrostyrenes

Dedicated to Professor Dieter Enders on the occasion of his 70^th birthday

Abstract

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

Key words

dihydrofurans - organocatalysis - domino Michael/alkylation - Takemoto catalyst - (Z)-β-chloro-β-nitrostyrenes

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