Literature DB >> 12940733

Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines.

Wen-Bo Wang1, Sheng-Mei Lu, Peng-Yu Yang, Xiu-Wen Han, Yong-Gui Zhou.   

Abstract

The highly enantioselective hydrogenation of quinoline derivatives is developed using [Ir(COD)Cl]2/(R)-MeO-Biphep/I2 system, and this methodology has been applied to the asymmetric synthesis of three naturally occurring alkaloids angustureine, galipinine, and cuspareine. This method provided an efficient access to a variety of optically active tetrahydroquinolines with up to 96% ee.

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Year:  2003        PMID： 12940733     DOI： 10.1021/ja0353762

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


  12 in total

1.  Dirhodium-catalyzed C-H arene amination using hydroxylamines.

Authors:  Mahesh P Paudyal; Adeniyi Michael Adebesin; Scott R Burt; Daniel H Ess; Zhiwei Ma; László Kürti; John R Falck
Journal:  Science       Date:  2016-09-09       Impact factor: 47.728

2.  Enantioselective Synthesis of Tetrahydroquinolines, Tetrahydroquinoxalines, and Tetrahydroisoquinolines via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  B A Hopkins; J P Wolfe
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

3.  Transformation of N, N-Dimethylaniline N-Oxides into Diverse Tetrahydroquinoline Scaffolds via Formal Povarov Reactions.

Authors:  Timothy S Bush; Glenn P A Yap; William J Chain
Journal:  Org Lett       Date:  2018-08-15       Impact factor: 6.005

4.  Enantioselective, nickel-catalyzed Suzuki cross-coupling of quinolinium ions.

Authors:  Jason D Shields; Derek T Ahneman; Thomas J A Graham; Abigail G Doyle
Journal:  Org Lett       Date:  2013-11-26       Impact factor: 6.005

5.  Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis.

Authors:  Patrick D Parker; Xintong Hou; Vy M Dong
Journal:  J Am Chem Soc       Date:  2021-04-23       Impact factor: 16.383

6.  An intramolecular C-N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis.

Authors:  Hana Doušová; Radim Horák; Zdeňka Růžičková; Petr Šimůnek
Journal:  Beilstein J Org Chem       Date:  2015-05-27       Impact factor: 2.883

7.  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

8.  Catalytic asymmetric hydrogenation of 3-substituted benzisoxazoles.

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

9.  A supramolecularly tunable chiral diphosphine ligand: application to Rh and Ir-catalyzed enantioselective hydrogenation.

Authors:  Xi-Chang Zhang; Yi-Hu Hu; Chuan-Fu Chen; Qiang Fang; Li-Yao Yang; Ying-Bo Lu; Lin-Jie Xie; Jing Wu; Shijun Li; Wenjun Fang
Journal:  Chem Sci       Date:  2016-03-31       Impact factor: 9.825

Review 10.  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
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