Literature DB >> 23957763

Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Weiwei Zi1, F Dean Toste.   

Abstract

A highly enantioselective carboalkoxylation of alkynes catalyzed by cationic (DTBM-MeO-Biphep)gold(I) complexes is reported. Various optically active β-alkoxyindanone derivatives were obtained in good yields with high enantioselectivities. Furthermore, this methodology was extended to the enantioselective synthesis of 3-methoxycyclopentenones. The reaction is proposed to proceed through an enantioselective cyclization of intermediates containing vinylgold(I) and prochiral oxocarbenium moieties.

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Year:  2013        PMID： 23957763      PMCID： PMC3795527          DOI： 10.1021/ja407150h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  44 in total

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5.  Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

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Journal:  J Am Chem Soc       Date:  2012-05-29       Impact factor: 15.419

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Authors:  Pascal Dubé; F Dean Toste
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

7.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
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8.  Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds.

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9.  Catalytic asymmetric addition of aldehydes to oxocarbenium ions: a dual catalytic system for the synthesis of chromenes.

Authors:  Magnus Rueping; Chandra M R Volla; Iuliana Atodiresei
Journal:  Org Lett       Date:  2012-08-22       Impact factor: 6.005

10.  Generation and trapping of cyclopentenylidene gold species: four pathways to polycyclic compounds.

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Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419
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  8 in total

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3.  Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis.

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4.  A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.

Authors:  Mark A Maskeri; Matthew J O'Connor; Ashley A Jaworski; Anna V Bay; Karl A Scheidt
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5.  Rh-catalyzed Reagent-Free Ring Expansion of Cyclobutenones and Benzocyclobutenones.

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6.  Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.

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7.  One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes.

Authors:  Laurence Burroughs; Lee Eccleshare; John Ritchie; Omkar Kulkarni; Barry Lygo; Simon Woodward; William Lewis
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8.  1,2-N-migration in a gold-catalysed synthesis of functionalised indenes by the 1,1-carboalkoxylation of ynamides.

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  8 in total

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