Literature DB >> 16550297

Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts.

Svetlana B Tsogoeva1, Shengwei Wei.   

Abstract

A new and effective organocatalytic system: primary amine derived chiral thiourea catalyst and AcOH-H2O additive, which converts different ketones to gamma-nitroketones in high yields (82-99%) and enantioselectivities (90-99%) has been described.

Entities:  

Year:  2006        PMID： 16550297     DOI： 10.1039/b517937h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

1.  Free energy profile and microkinetic modeling of base-catalyzed conjugate addition reaction of nitroalkanes to α,β-unsaturated ketones in polar and apolar solvents.

Authors:  Virginia C Rufino; Stella M Resende; Josefredo R Pliego
Journal:  J Mol Model       Date:  2018-06-07       Impact factor: 1.810

2.  Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway.

Authors:  Adam R Brown; Wen-Hsin Kuo; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

3.  Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

Authors:  Mathieu P Lalonde; Meredeth A McGowan; Naomi S Rajapaksa; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-01-28       Impact factor: 15.419

4.  Synthesis of Prolinal Dithioacetals as Catalysts for the Highly Stereoselective Michael Addition of Ketones and Aldehydes to beta-Nitrostyrenes.

Authors:  Tanmay Mandal; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2007       Impact factor: 2.415

5.  Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters.

Authors:  Adam D Gammack Yamagata; Swarup Datta; Kelvin E Jackson; Linus Stegbauer; Robert S Paton; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336

6.  The Cyanation of Prochiral Aldehydes with Chiral Copper Complexes of R-(+)/S-(-) -α-Ethylphenyl Amine in Methanol.

Authors:  Luo Mei
Journal:  Curr Org Synth       Date:  2016-06       Impact factor: 1.975

7.  A New Organocatalytic Desymmetrization Reaction Enables the Enantioselective Total Synthesis of Madangamine E.

Authors:  Shinya Shiomi; Benjamin D A Shennan; Ken Yamazaki; Ángel L Fuentes de Arriba; Dhananjayan Vasu; Trevor A Hamlin; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2022-01-17       Impact factor: 15.419

8.  Direct β-selectivity of α,β-unsaturated γ-butyrolactam for asymmetric conjugate additions in an organocatalytic manner.

Authors:  Yuan Zhong; Sihua Hong; Zhengjun Cai; Shixiong Ma; Xianxing Jiang
Journal:  RSC Adv       Date:  2018-08-14       Impact factor: 4.036
  8 in total

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