Literature DB >> 27376625

Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis.

Stephen E Ammann1, Wei Liu1, M Christina White2.   

Abstract

The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C-H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C-H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee, 13 examples with greater than 90 % ee).
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; S ligands; asymmetric catalysis; oxidation; palladium

Mesh：

Substances：

Year:  2016        PMID： 27376625      PMCID： PMC5729747          DOI： 10.1002/anie.201603576

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


  35 in total

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Authors:  Zhuo Chai; Trevor J Rainey
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3.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

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Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

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5.  A new class of non-C2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones.

Authors:  Barry M Trost; Etienne J Donckele; David A Thaisrivongs; Maksim Osipov; James T Masters
Journal:  J Am Chem Soc       Date:  2015-02-16       Impact factor: 15.419

6.  Catalytic enantioselective oxidative cross-coupling of benzylic ethers with aldehydes.

Authors:  Zhilin Meng; Shutao Sun; Huiqing Yuan; Hongxiang Lou; Lei Liu
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-07       Impact factor: 15.336

7.  Catalytic Allylic Oxidation of Alkenes Using an Asymmetric Kharasch-Sosnovsky Reaction.

Authors:  Jason Eames; Michael Watkinson
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-01       Impact factor: 15.336

8.  Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate.

Authors:  Merritt B Andrus; Ziniu Zhou
Journal:  J Am Chem Soc       Date:  2002-07-31       Impact factor: 15.419

Review 9.  Understanding Palladium Acetate from a User Perspective.

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Journal:  Chemistry       Date:  2016-04-29       Impact factor: 5.236

10.  Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation.

Authors:  Stephen E Ammann; Grant T Rice; M Christina White
Journal:  J Am Chem Soc       Date:  2014-07-16       Impact factor: 15.419
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Authors:  Wei Liu; Siraj Z Ali; Stephen E Ammann; M Christina White
Journal:  J Am Chem Soc       Date:  2018-08-17       Impact factor: 15.419

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5.  Synthesis of anti-1,3 Amino Alcohol Motifs via Pd(II)/SOX Catalysis with the Capacity for Stereodivergence.

Authors:  Rulin Ma; Jonathon Young; Rossella Promontorio; Friederike M Dannheim; Christopher C Pattillo; M Christina White
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6.  Catalytic Asymmetric Intermolecular Allylic Functionalization of Unactivated Internal Alkenes.

Authors:  Liela Bayeh; Uttam K Tambar
Journal:  ACS Catal       Date:  2017-10-27       Impact factor: 13.084

7.  Pd-catalyzed asymmetric allylic alkylations via C-H activation of N-allyl imines with glycinates.

Authors:  Barry M Trost; Xiaoxun Li
Journal:  Chem Sci       Date:  2017-08-15       Impact factor: 9.825

8.  Selective C(sp3 )-H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow.

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9.  Cobalt-catalyzed nucleophilic addition of the allylic C(sp3)-H bond of simple alkenes to ketones.

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10.  An integrated screening system for the selection of exemplary substrates for natural and engineered cytochrome P450s.

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