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Literature DB >> 25298286

Rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes.

Changkun Li¹, Matthias Kähny, Bernhard Breit.

Abstract

A rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes to give branched N-allyl 2-pyridones is reported. Preliminary mechanistic studies support the hypothesis that the reaction was initiated from the more acidic 2-hydroxypyridine form, and the initial kinetic O-allylation product was finally converted into the thermodynamically more stable N-allyl 2-pyridones.

Entities: Chemical

Keywords: 2-pyridones; allenes; asymmetric allylation; reaction mechanisms; rhodium

Mesh：

Substances：

Year: 2014 PMID： 25298286 DOI： 10.1002/anie.201407935

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

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Cited

7 in total

1. Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

Authors: Qing-An Chen; Zhiwei Chen; Vy M Dong
Journal: J Am Chem Soc Date: 2015-06-29 Impact factor: 15.419

2. Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors: Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal: J Am Chem Soc Date: 2019-05-15 Impact factor: 15.419

3. Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

Authors: Dimitri A Khrakovsky; Chuanzhou Tao; Miles W Johnson; Richard T Thornbury; Sophia L Shevick; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2016-04-20 Impact factor: 15.336

4. Regioselectivity and Mechanism of Synthesizing N-Substituted 2-Pyridones and 2-Substituted Pyridines via Metal-Free C-O and C-N Bond-Cleaving of Oxazoline[3,2-a]pyridiniums.

Authors: Bo Li; Susu Xue; Yang Yang; Jia Feng; Peng Liu; Yong Zhang; Jianming Zhu; Zhijian Xu; Adrian Hall; Bo Zhao; Jiye Shi; Weiliang Zhu
Journal: Sci Rep Date: 2017-01-25 Impact factor: 4.379

Rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes.

1. Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

2. Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

3. Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

4. Regioselectivity and Mechanism of Synthesizing N-Substituted 2-Pyridones and 2-Substituted Pyridines via Metal-Free C-O and C-N Bond-Cleaving of Oxazoline[3,2-a]pyridiniums.

5. Rhodium-NHC-Catalyzed gem-Specific O-Selective Hydropyridonation of Terminal Alkynes.

6. Bis-Phosphaketenes LM(PCO)₂ (M=Ga, In): A New Class of Reactive Group 13 Metal-Phosphorus Compounds.

7. Asymmetric synthesis of allylic amines via hydroamination of allenes with benzophenone imine.