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Literature DB >> 20552968

Pd-catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids.

Duo-Sheng Wang¹, Qing-An Chen, Wei Li, Chang-Bin Yu, Yong-Gui Zhou, Xumu Zhang.

Abstract

The first highly enantioselective hydrogenation of simple indoles was developed with a Brønsted acid as an activator to form the iminium intermediate in situ, which was hydrogenated using Pd(OCOCF(3))(2)/(R)-H8-BINAP catalyst system with up to 96% ee. The present method provides an efficient route to enantioenriched 2-substituted and 2,3-disubstituted indolines.

Entities: Chemical

Mesh：

Substances：
Indoles
Palladium

Year: 2010 PMID： 20552968 DOI： 10.1021/ja103668q

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

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Cited

12 in total

1. Dynamic Kinetic Resolution of Aldehydes by Hydroacylation.

Authors: Zhiwei Chen; Yusuke Aota; Hillary M H Nguyen; Vy M Dong
Journal: Angew Chem Int Ed Engl Date: 2019-02-27 Impact factor: 15.336

2. 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

3. 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

4. Heterogeneous catalytic hydrogenation of unprotected indoles in water: a green solution to a long-standing challenge.

Authors: Aditya Kulkarni; Weihong Zhou; Béla Török
Journal: Org Lett Date: 2011-09-08 Impact factor: 6.005

5. Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors: Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal: Chem Rev Date: 2017-02-06 Impact factor: 60.622

Pd-catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids.

1. Dynamic Kinetic Resolution of Aldehydes by Hydroacylation.

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

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

4. Heterogeneous catalytic hydrogenation of unprotected indoles in water: a green solution to a long-standing challenge.

5. Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

6. Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

7. Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination.

8. Direct, Enantioselective Synthesis of Pyrroloindolines and Indolines From Simple Indole Derivatives.

9. Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines.

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