Literature DB >> 19322862

The fluorine-iminium ion gauche effect: proof of principle and application to asymmetric organocatalysis.

Christof Sparr1, W Bernd Schweizer, Hans Martin Senn, Ryan Gilmour.   

Abstract

The gauche effect that is induced upon reversible formation of an iminium ion (see structure: green F, blue N) provides a powerful method for the preorganization of transient intermediates that are central to secondary amine catalyzed processes. This phenomenon has been exploited in the design of a novel organocatalyst and is showcased in the stereoselective epoxidation of alpha,beta-unsaturated aldehydes.

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Year:  2009        PMID： 19322862     DOI： 10.1002/anie.200900405

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Isotope Effects Reveal an Alternative Mechanism for "Iminium-Ion" Catalysis.

Authors:  Joseph A Izzo; Pernille H Poulsen; Jeremy A Intrator; Karl Anker Jørgensen; Mathew J Vetticatt
Journal:  J Am Chem Soc       Date:  2018-06-29       Impact factor: 15.419

2.  The C-F bond as a conformational tool in organic and biological chemistry.

Authors:  Luke Hunter
Journal:  Beilstein J Org Chem       Date:  2010-04-20       Impact factor: 2.883

3.  H12461. Fluorine as a Regiocontrol Element in the Ring Openings of Bicyclic Aziridiniums.

Authors:  Yu-Hong Lam; Kendall N Houk; Janine Cossy; Domingo Gomez Prado; Anne Cochi
Journal:  Helv Chim Acta       Date:  2012-11-19       Impact factor: 2.164

4.  Catalytic asymmetric intermolecular stetter reaction of heterocyclic aldehydes with nitroalkenes: backbone fluorination improves selectivity.

Authors:  Daniel A DiRocco; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

Review 5.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

6.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

7.  Origin of rate enhancement and asynchronicity in iminium catalyzed Diels-Alder reactions.

Authors:  Pascal Vermeeren; Trevor A Hamlin; Israel Fernández; F Matthias Bickelhaupt
Journal:  Chem Sci       Date:  2020-07-09       Impact factor: 9.825

8.  Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions.

Authors:  KyungA Lee; Daniel L Silverio; Sebastian Torker; Daniel W Robbins; Fredrik Haeffner; Farid W van der Mei; Amir H Hoveyda
Journal:  Nat Chem       Date:  2016-05-23       Impact factor: 24.427
  8 in total

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