Literature DB >> 22103563

Copper-catalyzed intramolecular hydroalkoxylation of α-(1-hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-endo mode for preparation of 2-alkyl- and 2-aryl-2,5-dihydrofurans.

Sanghyuck Kim1, Phil Ho Lee.   

Abstract

Ethyl α-(1-hydroxy-1-alkyl)methylallenoates and α-(1-hydroxy-1-aryl)methylallenoates containing not only electron-donating groups but also an electron-withdrawing group on the aryl group at the α-position have been shown to undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbonyl-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.

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Year:  2011        PMID: 22103563     DOI: 10.1021/jo2018125

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.

Authors:  Barbara J Casavant; Zainab M Khoder; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2015-12-01       Impact factor: 6.005

Review 2.  Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates.

Authors:  Alexander P Pulis; Kay Yeung; David J Procter
Journal:  Chem Sci       Date:  2017-06-08       Impact factor: 9.825

Review 3.  First-Row Late Transition Metals for Catalytic Alkene Hydrofunctionalisation: Recent Advances in C-N, C-O and C-P Bond Formation.

Authors:  Sophie Bezzenine-Lafollée; Richard Gil; Damien Prim; Jérôme Hannedouche
Journal:  Molecules       Date:  2017-11-04       Impact factor: 4.411

  3 in total

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