Literature DB >> 15387619

Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts.

Eun Joo Park1, Mi Hee Kim, Dae Young Kim.   

Abstract

Catalytic enantioselective alkylation promoted by a quaternary ammonium salt from cinchonine as a phase transfer catalyst is described. Treatment of cyclo beta-keto esters with alkyl halide under mild reaction conditions afforded the corresponding alpha-alkylated beta-keto esters in moderate to excellent yields with high enantiomeric excesses Copyright 2004 American Chemical Society

Entities:  

Year:  2004        PMID: 15387619     DOI: 10.1021/jo0401772

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


  10 in total

1.  Radical-Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes.

Authors:  John A Milligan; Kevin L Burns; Anthony V Le; Viktor C Polites; Zheng-Jun Wang; Gary A Molander; Christopher B Kelly
Journal:  Adv Synth Catal       Date:  2019-11-08       Impact factor: 5.837

2.  Catalytic enantioselective claisen rearrangements of O-allyl β-ketoesters.

Authors:  Christopher Uyeda; Andreas R Rötheli; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-10       Impact factor: 15.336

3.  Catalytic asymmetric alkylation of substituted isoflavanones.

Authors:  Antoinette E Nibbs; Amanda-Lauren Baize; Rachel M Herter; Karl A Scheidt
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

4.  Study of cyclic quaternary ammonium bromides by B3LYP calculations, NMR and FTIR spectroscopies.

Authors:  Bogumił Brycki; Adrianna Szulc; Iwona Kowalczyk
Journal:  Molecules       Date:  2010-08-16       Impact factor: 4.411

5.  Synthesis, spectroscopic and semiempirical studies of new quaternary alkylammonium conjugates of sterols.

Authors:  Bogumił Brycki; Hanna Koenig; Iwona Kowalczyk; Tomasz Pospieszny
Journal:  Molecules       Date:  2013-12-05       Impact factor: 4.411

6.  Synthesis, molecular structure, spectral properties and antifungal activity of polymethylene-α,ω-bis(N,N- dimethyl-N-dodecyloammonium bromides).

Authors:  Bogumil Brycki; Iwona Kowalczyk; Anna Kozirog
Journal:  Molecules       Date:  2011-01-05       Impact factor: 4.411

7.  Enantioselective Michael addition of 3-aryl-substituted oxindoles to methyl vinyl ketone catalyzed by a binaphthyl-modified bifunctional organocatalyst.

Authors:  Hyun Joo Lee; Saet Byeol Woo; Dae Young Kim
Journal:  Molecules       Date:  2012-06-18       Impact factor: 4.411

8.  H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters.

Authors:  Patryk Niedbała; Maciej Majdecki; Piotr Grodek; Janusz Jurczak
Journal:  Molecules       Date:  2022-04-13       Impact factor: 4.927

9.  (2S,7S)-10-Ethyl-1,8,10,12-tetra-aza-tetra-cyclo-[8.3.1.1(8,12).0(2,7)]penta-decan-10-ium iodide.

Authors:  Augusto Rivera; Héctor Jairo Osorio; John Sadat-Bernal; Václav Eigner; Michal Dušek
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-29

10.  Enantioselective Synthesis of Acyclic Orthogonally Functionalized Compounds Bearing a Quaternary Stereocenter Using Chiral Ammonium Salt Catalysis.

Authors:  Katharina Röser; Bettina Berger; Michael Widhalm; Mario Waser
Journal:  ChemistryOpen       Date:  2021-08       Impact factor: 2.630

  10 in total

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