Literature DB >> 18422288

Asymmetric transfer hydrogenation of beta,gamma-alkynyl alpha-imino esters by a Brønsted acid.

Qiang Kang1, Zhuo-An Zhao, Shu-Li You.   

Abstract

Asymmetric synthesis of trans-alkenyl alpha-amino esters was realized by chiral phosphoric acid catalyzed transfer hydrogenation of beta,gamma-alkynyl alpha-imino esters. Utilizing Hantzsch esters as the hydrogen donor, both the alkyne and imine moieties of beta,gamma-alkynyl alpha-imino esters were reduced to afford trans-alkenyl alpha-amino esters with up to 96% ee.

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Year:  2008        PMID： 18422288     DOI： 10.1021/ol800494r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.

Authors:  Christopher G Evans; Jason E Gestwicki
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

2.  Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids.

Authors:  Guilong Li; Jon C Antilla
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

3.  Enantioselective synthesis of α-alkenyl α-amino acids via N-H insertion reactions.

Authors:  Jun-Xia Guo; Ting Zhou; Bin Xu; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2015-10-28       Impact factor: 9.825

4.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

5.  Brønsted acid catalysis - the effect of 3,3'-substituents on the structural space and the stabilization of imine/phosphoric acid complexes.

Authors:  Maxime Melikian; Johannes Gramüller; Johnny Hioe; Julian Greindl; Ruth M Gschwind
Journal:  Chem Sci       Date:  2019-04-08       Impact factor: 9.825

6.  Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3'-substituents in Brønsted acid catalysis.

Authors:  Kerstin Rothermel; Maxime Melikian; Johnny Hioe; Julian Greindl; Johannes Gramüller; Matej Žabka; Nils Sorgenfrei; Thomas Hausler; Fabio Morana; Ruth M Gschwind
Journal:  Chem Sci       Date:  2019-09-06       Impact factor: 9.825

7.  Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction.

Authors:  Yiwen Xiong; Haibo Mei; Lingmin Wu; Jianlin Han; Yi Pan; Guigen Li
Journal:  Beilstein J Org Chem       Date:  2014-03-13       Impact factor: 2.883

8.  Relaxation Dispersion NMR to Reveal Fast Dynamics in Brønsted Acid Catalysis: Influence of Sterics and H-Bond Strength on Conformations and Substrate Hopping.

Authors:  N Lokesh; Johnny Hioe; Johannes Gramüller; Ruth M Gschwind
Journal:  J Am Chem Soc       Date:  2019-10-04       Impact factor: 15.419
  8 in total

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