Literature DB >> 21800916

Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.

James A Birrell1, Jean-Nicolas Desrosiers, Eric N Jacobsen.   

Abstract

A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful α,α-disubstituted butyrolactone products. This transformation is promoted by a new thiourea catalyst and 4-pyrrolidinopyridine and represents the first example of enantioselective thiourea anion-binding catalysis with fluoride.

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Year:  2011        PMID： 21800916      PMCID： PMC3164931          DOI： 10.1021/ja205602j

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


  29 in total

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4.  Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile.

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6.  The DMAP-catalyzed acetylation of alcohols--a mechanistic study (DMAP = 4-(dimethylamino)pyridine).

Authors:  Shangjie Xu; Ingmar Held; Bernhard Kempf; Herbert Mayr; Wolfgang Steglich; Hendrik Zipse
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7.  Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones.

Authors:  Dirk J Spielvogel; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-04-10       Impact factor: 15.419

8.  N-Heterocyclic carbene-catalyzed (4+2) cycloaddition/decarboxylation of silyl dienol ethers with α,β-unsaturated acid fluorides.

Authors:  Sarah J Ryan; Lisa Candish; David W Lupton
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9.  Origin of enantioselectivity in CF3-PIP-catalyzed kinetic resolution of secondary benzylic alcohols.

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10.  Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine.

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Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384
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  29 in total

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Review 6.  The Cation-π Interaction in Small-Molecule Catalysis.

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7.  Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

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8.  Switchable regioselectivity in amine-catalysed asymmetric cycloadditions.

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9.  Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

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10.  Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

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