Literature DB >> 15969570

Catalytic asymmetric hydrogenation of N-iminopyridinium ylides: expedient approach to enantioenriched substituted piperidine derivatives.

Claude Y Legault1, André B Charette.   

Abstract

We have developed an efficient catalytic enantioselective hydrogenation of pyridine derivatives. Enhanced reactivity was possible by an optimization of the electronic properties of the catalyst through ligand modification. This methodology shows the particular reactivity of N-iminopyridinium ylides that provides access to substituted piperidines in good enantiomeric excesses.

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Year:  2005        PMID： 15969570     DOI： 10.1021/ja0525298

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor.

Authors:  Xudong Wei; Bo Qu; Xingzhong Zeng; Jolaine Savoie; Keith R Fandrick; Jean-Nicolas Desrosiers; Sergei Tcyrulnikov; Maurice A Marsini; Frederic G Buono; Zhibin Li; Bing-Shiou Yang; Wenjun Tang; Nizar Haddad; Osvaldo Gutierrez; Jun Wang; Heewon Lee; Shengli Ma; Scot Campbell; Jon C Lorenz; Matthias Eckhardt; Frank Himmelsbach; Stefan Peters; Nitinchandra D Patel; Zhulin Tan; Nathan K Yee; Jinhua J Song; Frank Roschangar; Marisa C Kozlowski; Chris H Senanayake
Journal:  J Am Chem Soc       Date:  2016-11-17       Impact factor: 15.419

2.  Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.

Authors:  Bo Qu; Hari P R Mangunuru; Sergei Tcyrulnikov; Daniel Rivalti; Olga V Zatolochnaya; Dmitry Kurouski; Suttipol Radomkit; Soumik Biswas; Shuklendu Karyakarte; Keith R Fandrick; Joshua D Sieber; Sonia Rodriguez; Jean-Nicolas Desrosiers; Nizar Haddad; Keith McKellop; Scott Pennino; Heewon Lee; Nathan K Yee; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2018-02-20       Impact factor: 6.005

3.  PREPARATION OF (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro- (4S)-).

Authors:  Michael R Krout; Justin T Mohr; Brian M Stoltz
Journal:  Organic Synth       Date:  2009-01-01

4.  Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers.

Authors:  Zhang-Pei Chen; Mu-Wang Chen; Lei Shi; Chang-Bin Yu; Yong-Gui Zhou
Journal:  Chem Sci       Date:  2015-03-31       Impact factor: 9.825

5.  Catalytic asymmetric hydrogenation of 3-substituted benzisoxazoles.

Authors:  Ryuhei Ikeda; Ryoichi Kuwano
Journal:  Molecules       Date:  2012-06-06       Impact factor: 4.411

6.  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

7.  Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor.

Authors:  Yuki Naito; Naoki Shida; Mahito Atobe
Journal:  Beilstein J Org Chem       Date:  2022-03-29       Impact factor: 2.883

Review 8.  Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles.

Authors:  Mario P Wiesenfeldt; Zackaria Nairoukh; Toryn Dalton; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-29       Impact factor: 15.336
  8 in total

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