Literature DB >> 22174974

Highly Enantioselective Asymmetric Darzens Reactions with a Phase Transfer Catalyst.

Yan Liu1, Brian A Provencher, Keith J Bartleson, Li Deng.   

Abstract

A class of easily accessible and readily tunable chiral phase transfer catalysts based on 6'-OH cinchonium salts was found to efficiently catalyze an unprecedented highly enantioselective Darzens reaction of α-chloro ketones and aldehydes, which directly produces optically active chiral epoxides from readily available carbonyl compounds.

Entities:  

Year:  2011        PMID： 22174974      PMCID： PMC3235651          DOI： 10.1039/c1sc00137j

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  21 in total

1.  Organocatalytic asymmetric cyanosilylation of nitroalkenes.

Authors:  Pablo Bernal; Rosario Fernández; José M Lassaletta
Journal:  Chemistry       Date:  2010-07-12       Impact factor: 5.236

2.  Construction of quaternary stereocenters by efficient and practical conjugate additions to alpha,beta-unsaturated ketones with a chiral organic catalyst.

Authors:  Fanghui Wu; Hongming Li; Ran Hong; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-30       Impact factor: 15.336

3.  Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

Authors:  Hongming Li; Baomin Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

4.  Control of diastereoselectivity in tandem asymmetric reactions generating nonadjacent stereocenters with bifunctional catalysis by cinchona alkaloids.

Authors:  Baomin Wang; Fanghui Wu; Yi Wang; Xiaofeng Liu; Li Deng
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

5.  Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones.

Authors:  Hongming Li; Jun Song; Xiaofeng Liu; Li Deng
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

6.  Chiral bifunctional phase transfer catalysts for asymmetric fluorination of beta-keto esters.

Authors:  Xisheng Wang; Quan Lan; Seiji Shirakawa; Keiji Maruoka
Journal:  Chem Commun (Camb)       Date:  2009-11-27       Impact factor: 6.222

7.  Catalytic enantioselective aza-Henry reaction with broad substrate scope.

Authors:  Claudio Palomo; Mikel Oiarbide; Antonio Laso; Rosa López
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

8.  Phase transfer catalyzed enantioselective Strecker reactions of alpha-amido sulfones with cyanohydrins.

Authors:  Raquel P Herrera; Valentina Sgarzani; Luca Bernardi; Francesco Fini; Daniel Pettersen; Alfredo Ricci
Journal:  J Org Chem       Date:  2006-12-22       Impact factor: 4.354

9.  Enantioselective base-free phase-transfer reaction in water-rich solvent.

Authors:  Rongjun He; Seiji Shirakawa; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

Review 10.  Asymmetric catalysis by chiral hydrogen-bond donors.

Authors:  Mark S Taylor; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-27       Impact factor: 15.336
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  10 in total

1.  Structural study-guided development of versatile phase-transfer catalysts for asymmetric conjugate additions of cyanide.

Authors:  Brian A Provencher; Keith J Bartelson; Yan Liu; Bruce M Foxman; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-14       Impact factor: 15.336

2.  Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts.

Authors:  Mario Waser; Katharina Gratzer; Richard Herchl; Norbert Müller
Journal:  Org Biomol Chem       Date:  2011-10-31       Impact factor: 3.876

3.  Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (-)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents.

Authors:  K C Nicolaou; Guodu Liu; Kathryn Beabout; Megan D McCurry; Yousif Shamoo
Journal:  J Am Chem Soc       Date:  2017-03-03       Impact factor: 15.419

4.  Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines.

Authors:  Xiao Zhou; Yongwei Wu; Li Deng
Journal:  J Am Chem Soc       Date:  2016-09-09       Impact factor: 15.419

5.  Asymmetric cyclopropanation of chalcones using chiral phase-transfer catalysts.

Authors:  Richard Herchl; Mario Waser
Journal:  Tetrahedron Lett       Date:  2013-05-15       Impact factor: 2.415

6.  Na@SiO2-Mediated Addition of Organohalides to Carbonyl Compounds for the Formation of Alcohols and Epoxides.

Authors:  Mohit Kapoor; Jih Ru Hwu
Journal:  Sci Rep       Date:  2016-11-17       Impact factor: 4.379

7.  An Entry to Enantioenriched 3,3-Disubstituted Phthalides through Asymmetric Phase-Transfer-Catalyzed γ-Alkylation.

Authors:  Marina Sicignano; Rosaria Schettini; Giovanni Pierri; Maria Leda Marino; Irene Izzo; Francesco De Riccardis; Luca Bernardi; Giorgio Della Sala
Journal:  J Org Chem       Date:  2020-05-27       Impact factor: 4.354

8.  Highly Efficient Darzens Reactions Mediated by Phosphazene Bases under Mild Conditions.

Authors:  Carmine Lops; Paolo Pengo; Lucia Pasquato
Journal:  ChemistryOpen       Date:  2022-10       Impact factor: 2.630

9.  Application scope and limitations of TADDOL-derived chiral ammonium salt phase-transfer catalysts.

Authors:  Guddeangadi N Gururaja; Richard Herchl; Antonia Pichler; Katharina Gratzer; Mario Waser
Journal:  Molecules       Date:  2013-04-12       Impact factor: 4.411

Review 10.  Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Authors:  Johannes Schörgenhumer; Maximilian Tiffner; Mario Waser
Journal:  Beilstein J Org Chem       Date:  2017-08-22       Impact factor: 2.883
  10 in total

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