Literature DB >> 10880217

General asymmetric hydrogenation of hetero-aromatic ketones

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Abstract

trans-RuCl(2)[(R)-xylbinap][(R)-daipen] or the S,S complex acts as an efficient catalyst for asymmetric hydrogenation of hetero-aromatic ketones. The hydrogenation proceeds with a substrate-to-catalyst molar ratio of 1000-40000 to give chiral alcohols in high ee and high yield. The enantioselectivity appears to be little affected by the properties of the hetero-aromatic ring. This method allows for asymmetric synthesis of duloxetine, an inhibitor of serotonin and norepinephrine uptake carriers.

Entities:  

Year:  2000        PMID: 10880217     DOI: 10.1021/ol0000814

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Toward efficient asymmetric hydrogenation: architectural and functional engineering of chiral molecular catalysts.

Authors:  Ryoji Noyori; Masato Kitamura; Takeshi Ohkuma
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-19       Impact factor: 11.205

2.  Short and efficient synthetic route to methyl α-trioxacarcinoside B and anomerically activated derivatives.

Authors:  Thomas Magauer; Andrew G Myers
Journal:  Org Lett       Date:  2011-09-29       Impact factor: 6.005

3.  Asymmetric hydrosilylation of ketones catalyzed by complexes formed from trans-diaminocyclohexane-based diamines and diethylzinc.

Authors:  Jadwiga Gajewy; Jacek Gawronski; Marcin Kwit
Journal:  Monatsh Chem       Date:  2012-04-18       Impact factor: 1.451

4.  Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones.

Authors:  Viatcheslav Stepanenko; Melvin De Jesús; Wildeliz Correa; Lorianne Bermúdez; Cindybeth Vázquez; Irisbel Guzmán; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2009-12-11

5.  Ruthenium-catalyzed asymmetric hydrogenation of aromatic and heteroaromatic ketones using cinchona alkaloid-derived NNP ligands.

Authors:  Ling Zhang; Qian Chen; Linlin Li; Jian Jiang; Hao Sun; Li Li; Ting Liu; Lin Zhang; Chun Li
Journal:  RSC Adv       Date:  2022-05-18       Impact factor: 4.036

Review 6.  Asymmetric hydrogenation of ketones: tactics to achieve high reactivity, enantioselectivity, and wide scope.

Authors:  Takeshi Ohkuma
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2010       Impact factor: 3.493

7.  Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.

Authors:  Avene C Colgan; Rupert S J Proctor; David C Gibson; Padon Chuentragool; Antti S K Lahdenperä; Kristaps Ermanis; Robert J Phipps
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-27       Impact factor: 16.823

8.  Chemoenzymatic Asymmetric Synthesis of Pyridine-Based α-Fluorinated Secondary Alcohols.

Authors:  Timo Broese; Peter Ehlers; Peter Langer; Jan von Langermann
Journal:  Chembiochem       Date:  2021-10-07       Impact factor: 3.461

  8 in total

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