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Synthesis 2017; 49(01): 195-201
DOI: 10.1055/s-0035-1562446
DOI: 10.1055/s-0035-1562446
paper
Enantioselective Organocatalyzed Consecutive Synthesis of Alkyl 4,5-Dihydrofuran-2-carboxylates from α-Keto Esters and (Z)-β-Chloro-β-nitrostyrenes
Further Information
Publication History
Received: 26 May 2016
Accepted: 06 June 2016
Publication Date:
07 July 2016 (online)
Dedicated to Professor Dieter Enders on the occasion of his 70th 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-nitrostyrenesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562446.
- Supporting Information
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