Literature DB >> 22577004

Brønsted acid activation strategy in transition-metal catalyzed asymmetric hydrogenation of N-unprotected imines, enamines, and N-heteroaromatic compounds.

Zhengkun Yu1, Weiwei Jin, Quanbin Jiang.   

Abstract

Asymmetric hydrogenation plays an important role in organic synthesis, but that of the challenging substrates such as N-unprotected imines, enamines, and N-heteroaromatic compounds (1H-indoles, 1H-pyrroles, pyridines, quinolines, and quinoxalines) has only received increased attention in the past three years. Considering the interaction modes of a Brønsted acid with a Lewis base, Brønsted acids may be used as the ideal activators of C=N bonds. This Minireview summarizes the recent advances in transition-metal-catalyzed, Brønsted acid activated asymmetric hydrogenation of these challenging substrates, thus offering a promising substrate activation strategy for transformations involving C=N bonds.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22577004     DOI: 10.1002/anie.201200963

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  11 in total

1.  Iridium-catalyzed direct asymmetric reductive amination utilizing primary alkyl amines as the N-sources.

Authors:  Zitong Wu; Wenji Wang; Haodong Guo; Guorui Gao; Haizhou Huang; Mingxin Chang
Journal:  Nat Commun       Date:  2022-06-10       Impact factor: 17.694

2.  Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

Authors:  Qingyang Zhao; Jialin Wen; Renchang Tan; Kexuan Huang; Pedro Metola; Rui Wang; Eric V Anslyn; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-18       Impact factor: 15.336

Review 3.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

4.  Enantiomerically Pure Quinoline-Based κ-Opioid Receptor Agonists: Chemoenzymatic Synthesis and Pharmacological Evaluation.

Authors:  Benedikt Martin; Dirk Schepmann; Freddy A Bernal; Thomas J Schmidt; Tao Che; Karin Loser; Bernhard Wünsch
Journal:  ChemMedChem       Date:  2020-07-02       Impact factor: 3.466

5.  A robust iron catalyst for the selective hydrogenation of substituted (iso)quinolones.

Authors:  Basudev Sahoo; Carsten Kreyenschulte; Giovanni Agostini; Henrik Lund; Stephan Bachmann; Michelangelo Scalone; Kathrin Junge; Matthias Beller
Journal:  Chem Sci       Date:  2018-09-06       Impact factor: 9.825

6.  Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)-NHC-catalysed asymmetric hydrogenation of 2-oxazolones.

Authors:  Wei Li; Marco Wollenburg; Frank Glorius
Journal:  Chem Sci       Date:  2018-06-28       Impact factor: 9.825

7.  Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams.

Authors:  Tobias Wagener; Lukas Lückemeier; Constantin G Daniliuc; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-12       Impact factor: 15.336

8.  Catalytic Polymerization of Phthalonitrile Resins by Carborane with Enhanced Thermal Oxidation Resistance: Experimental and Molecular Simulation.

Authors:  Yuxiang Jia; Xiaojun Bu; Junyu Dong; Quan Zhou; Min Liu; Fang Wang; Maoyuan Wang
Journal:  Polymers (Basel)       Date:  2022-01-05       Impact factor: 4.329

9.  Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety.

Authors:  Andrej Šterman; Izidor Sosič; Zdenko Časar
Journal:  Chem Sci       Date:  2022-01-26       Impact factor: 9.825

10.  Strong Brønsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh-thiourea chiral phosphine complex via anion binding.

Authors:  Jialin Wen; Renchang Tan; Shaodong Liu; Qingyang Zhao; Xumu Zhang
Journal:  Chem Sci       Date:  2016-01-26       Impact factor: 9.825

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