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Issue 79, 2015
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A highly enantioselective, organocatalytic [3+2]-cycloannulation reaction towards the de novo-synthesis of 1-cyclopentenyl-α-keto esters

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Abstract

We disclose herein a highly enantioselective de novo-synthesis of chiral 1-cyclopentenyl-α-keto esters starting from a simple bis-silyl-1,3-dienediolate and α,β-unsaturated aldehydes via a domino vinylogous Michael-intramolecular Knoevenagel-type condensation. The cyclopentenes proved to be highly versatile and were readily converted into various structural motifs.

Graphical abstract: A highly enantioselective, organocatalytic [3+2]-cycloannulation reaction towards the de novo-synthesis of 1-cyclopentenyl-α-keto esters

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Publication details

The article was received on 17 Jul 2015, accepted on 14 Aug 2015 and first published on 14 Aug 2015


Article type: Communication
DOI: 10.1039/C5CC05967D
Chem. Commun., 2015,51, 14797-14800
  • Open access: Creative Commons BY license
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    A highly enantioselective, organocatalytic [3+2]-cycloannulation reaction towards the de novo-synthesis of 1-cyclopentenyl-α-keto esters

    P. R. Nareddy and C. Schneider, Chem. Commun., 2015, 51, 14797
    DOI: 10.1039/C5CC05967D

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