Literature DB >> 25297378

Asymmetric hydrogenation of pyridinium salts with an iridium phosphole catalyst.

Mingxin Chang1, Yuhua Huang, Shaodong Liu, Yonggang Chen, Shane W Krska, Ian W Davies, Xumu Zhang.   

Abstract

Iridium-catalyzed asymmetric hydrogenation of N-alkyl-2-alkylpyridinium salts provided 2-aryl-substituted piperidines with high levels of enantioselectivity. Simple benzyl and other alkyl groups successfully activated the challenging pyridine substrates toward hydrogenation. The use of the unusual chiral-phosphole-based MP(2) -SEGPHOS was the key to the success of this approach which provides a versatile and practical procedure for the synthesis of chiral piperidines.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; heterocycles; hydrogenation; iridium; stereoselectivity

Mesh：

Substances：

Year:  2014        PMID： 25297378     DOI： 10.1002/anie.201406762

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


  6 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.  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

4.  Pd-catalyzed asymmetric allylic substitution cascade using α-(pyridin-1-yl)-acetamides formed in situ as nucleophiles.

Authors:  Kun Yao; Qianjia Yuan; Xingxin Qu; Yangang Liu; Delong Liu; Wanbin Zhang
Journal:  Chem Sci       Date:  2018-12-04       Impact factor: 9.825

5.  Transition-Metal-Free Reductive Hydroxymethylation of Isoquinolines.

Authors:  Benjamin M Reeves; Hamish B Hepburn; Alexandru Grozavu; Peter J Lindsay-Scott; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336

6.  Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines.

Authors:  Mingxu Li; Jian Zhang; Yashi Zou; Fengfan Zhou; Zhenfeng Zhang; Wanbin Zhang
Journal:  Chem Sci       Date:  2021-10-28       Impact factor: 9.825
  6 in total

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