Literature DB >> 21553923

Iron-catalyzed asymmetric epoxidation of β,β-disubstituted enones.

Yasuhiro Nishikawa1, Hisashi Yamamoto.   

Abstract

The combination of Fe(OTf)(2) and novel phenanthroline ligands enables the catalytic asymmetric epoxidation of acyclic β,β-disubstituted enones, which have been a heretofore inaccessible substrate class. The reaction provides highly enantioenriched α,β-epoxyketones (up to 92% ee) that can be further converted to functionalized β-ketoaldehydes with an all-carbon quaternary center.

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Year:  2011        PMID： 21553923      PMCID： PMC3116448          DOI： 10.1021/ja201873d

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


  36 in total

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Review 3.  Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.

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Journal:  Chem Rev       Date:  2008-07-01       Impact factor: 60.622

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5.  Olefin cis-dihydroxylation versus epoxidation by non-heme iron catalysts: two faces of an Fe(III)-OOH coin.

Authors:  Kui Chen; Miquel Costas; Jinheung Kim; Adrianne K Tipton; Lawrence Que
Journal:  J Am Chem Soc       Date:  2002-03-27       Impact factor: 15.419

6.  Isoxazolines and isoxazoles as factor Xa inhibitors.

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7.  Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts.

Authors:  Waldemar Adam; Paraselli Bheema Rao; Hans-Georg Degen; Albert Levai; Tamás Patonay; Chantu R Saha-Möller
Journal:  J Org Chem       Date:  2002-01-11       Impact factor: 4.354

8.  Near-stoichiometric conversion of H(2)O(2) to Fe(IV)=O at a nonheme iron(II) center. Insights into the O-O bond cleavage step.

Authors:  Feifei Li; Jason England; Lawrence Que
Journal:  J Am Chem Soc       Date:  2010-02-24       Impact factor: 15.419

9.  Biomimetic iron-catalyzed asymmetric epoxidation of aromatic alkenes by using hydrogen peroxide.

Authors:  Feyissa Gadissa Gelalcha; Gopinathan Anilkumar; Man Kin Tse; Angelika Brückner; Matthias Beller
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Epoxidation and 1,2-dihydroxylation of alkenes by a nonheme iron model system - DFT supports the mechanism proposed by experiment.

Authors:  Peter Comba; Gopalan Rajaraman
Journal:  Inorg Chem       Date:  2007-12-12       Impact factor: 5.165
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  10 in total

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2.  Iron(II)-Catalyzed Asymmetric Epoxidation of Trisubstituted α,β-Unsaturated Esters.

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Journal:  European J Org Chem       Date:  2014-12

3.  Copper-Catalyzed Aerobic C-H Trifluoromethylation of Phenanthrolines.

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Journal:  Synlett       Date:  2015       Impact factor: 2.454

4.  Iron catalyzed asymmetric oxyamination of olefins.

Authors:  Kevin S Williamson; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

5.  Ten years of research in Chicago.

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Journal:  Tetrahedron       Date:  2013-06-10       Impact factor: 2.457

Review 6.  Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion.

Authors:  Alois Fürstner
Journal:  ACS Cent Sci       Date:  2016-10-27       Impact factor: 14.553

7.  Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.

Authors:  Deng-Fu Lu; Cheng-Liang Zhu; Zhen-Xin Jia; Hao Xu
Journal:  J Am Chem Soc       Date:  2014-09-16       Impact factor: 15.419

8.  Iron(II)-catalyzed asymmetric intramolecular olefin aminochlorination using chloride ion.

Authors:  Cheng-Liang Zhu; Jun-Shan Tian; Zhen-Yuan Gu; Guo-Wen Xing; Hao Xu
Journal:  Chem Sci       Date:  2015-03-13       Impact factor: 9.825

9.  A Bottom Up Approach Towards Artificial Oxygenases by Combining Iron Coordination Complexes and Peptides.

Authors:  Olaf Cusso; Michael W Giuliano; Xavi Ribas; Scott J Miller; Miquel Costas
Journal:  Chem Sci       Date:  2017-03-03       Impact factor: 9.825

10.  Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts.

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  10 in total

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