Literature DB >> 21837348

Direct enantioselective access to 4-substituted tetrahydroquinolines by catalytic asymmetric transfer hydrogenation of quinolines.

Magnus Rueping1, Thomas Theissmann, Mirjam Stoeckel, Andrey P Antonchick.   

Abstract

A convenient protocol for the enantioselective synthesis of 4-substituted tetrahydroquinolines has been developed. Chiral BINOL phosphoric acids promote the reduction of a wide range of 4-substituted quinolines with Hantzsch esters with good to high levels of enantioselectivity.

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Year:  2011        PMID： 21837348     DOI： 10.1039/c1ob05870c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  7 in total

1.  Self-Assembly of a Library of Polyborate Chiral Anions for Asymmetric Catalytic Quinoline Reduction.

Authors:  Aman A Desai; Yong Guan; Aaron L Odom; Supriyo Majumder; William D Wulff
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Synthesis of Structurally Diverse 3-, 4-, 5-, and 6-Membered Heterocycles from Diisopropyl Iminomalonates and Soft C-Nucleophiles.

Authors:  Padmanabha V Kattamuri; Urmibhusan Bhakta; Surached Siriwongsup; Doo-Hyun Kwon; Lawrence B Alemany; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal:  J Org Chem       Date:  2019-05-14       Impact factor: 4.354

3.  Phosphothreonine as a catalytic residue in peptide-mediated asymmetric transfer hydrogenations of 8-aminoquinolines.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-05       Impact factor: 15.336

4.  (4R)-4-(Biphenyl-4-yl)-7-chloro-1,2,3,4-tetra-hydro-quinoline.

Authors:  Thomas Theissmann; Michael Bolte
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-30

5.  Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis.

Authors:  Magnus Rueping; Teerawut Bootwicha; Erli Sugiono
Journal:  Beilstein J Org Chem       Date:  2012-02-23       Impact factor: 2.883

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.  A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines.

Authors:  Erli Sugiono; Magnus Rueping
Journal:  Beilstein J Org Chem       Date:  2013-11-13       Impact factor: 2.883
  7 in total

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