Literature DB >> 25623173

N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Anna Lee1, Karl A Scheidt.   

Abstract

A highly efficient asymmetric formal [4+2] annulation for the synthesis of dihydrocoumarins has been developed via an in situ activated NHC catalysis. Both electrophilic and nucleophilic species are generated in situ simultaneously whereby acyl imidazoles facilitated rapid formation of an NHC-enolate intermediate to afford the [4+2] dihydrocoumarin adducts.

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Year:  2015        PMID: 25623173      PMCID: PMC4331101          DOI: 10.1039/c4cc09590a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  50 in total

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4.  Enantioselective formation of substituted 3,4-dihydrocoumarins by a multicatalytic one-pot process.

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5.  N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

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6.  Organocatalytic Lewis base functionalisation of carboxylic acids, esters and anhydrides via C1-ammonium or azolium enolates.

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7.  Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine.

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8.  Enantioselective activation of stable carboxylate esters as enolate equivalents via N-heterocyclic carbene catalysts.

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9.  N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

Authors:  Eric M Phillips; Matthias Riedrich; Karl A Scheidt
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10.  Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to gamma-lactams.

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2.  A novel dihydrocoumarin under experimental and theoretical characterization.

Authors:  W F Vaz; J M F Custodio; N M N Rodrigues; L G Santin; S S Oliveira; R Gargano; F A P Osório; G L B Aquino; A J Camargo; M S Oliveira; H B Napolitano
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4.  Combined Photoredox and Carbene Catalysis for the Synthesis of γ-Aryloxy Ketones.

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Review 5.  Recent advances of N-heterocyclic carbenes in the applications of constructing carbo- and heterocyclic frameworks with potential biological activity.

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6.  NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.

Authors:  Alyn T Davies; Mark D Greenhalgh; Alexandra M Z Slawin; Andrew D Smith
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7.  A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation.

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Review 8.  Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry.

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  8 in total

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