通过N-烷氧基烯胺的极性翻转实现酮的亲核α-芳基化和α-烷基化：羰基化合物α-碳位置的极性转换反应研究 - Suppr

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Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: entry to the umpolung reaction at the α-carbon position of carbonyl compounds.

作者信息

Miyoshi Tetsuya, Miyakawa Takayuki, Ueda Masafumi, Miyata Okiko

机构信息

Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.

出版信息

Angew Chem Int Ed Engl. 2011 Jan 24;50(4):928-31. doi: 10.1002/anie.201004374. Epub 2010 Nov 23.

DOI:10.1002/anie.201004374

PMID:21246693

Abstract

摘要

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Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: entry to the umpolung reaction at the α-carbon position of carbonyl compounds.

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Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: entry to the umpolung reaction at the α-carbon position of carbonyl compounds.

作者信息

Miyoshi Tetsuya, Miyakawa Takayuki, Ueda Masafumi, Miyata Okiko

机构信息

Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.

出版信息

Angew Chem Int Ed Engl. 2011 Jan 24;50(4):928-31. doi: 10.1002/anie.201004374. Epub 2010 Nov 23.

DOI:10.1002/anie.201004374

PMID:21246693

Abstract

摘要

相似文献

Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: entry to the umpolung reaction at the α-carbon position of carbonyl compounds.

Angew Chem Int Ed Engl. 2011 Jan 24;50(4):928-31. doi: 10.1002/anie.201004374. Epub 2010 Nov 23.

Construction of a chiral quaternary carbon center by indium-catalyzed asymmetric alpha-alkenylation of beta-ketoesters.

J Am Chem Soc. 2008 Apr 2;130(13):4492-6. doi: 10.1021/ja710408f. Epub 2008 Mar 11.

Lewis acid-mediated rearrangement of activated cyclic amines: a facile synthetic protocol for the preparation of amino carbonyl compounds.

J Org Chem. 2007 Dec 21;72(26):10141-6. doi: 10.1021/jo702044k. Epub 2007 Nov 29.

Catalytic asymmetric Friedel-Crafts alkylation reactions--copper showed the way.

Chem Rev. 2008 Aug;108(8):2903-15. doi: 10.1021/cr078372e. Epub 2008 May 24.

Regioselectivity in the addition of vinylmagnesium bromide to heteroarylic ketones: C- versus O-alkylation.

J Org Chem. 2004 Dec 10;69(25):8903-9. doi: 10.1021/jo048948p.

Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple alpha,beta-unsaturated ketones.

Org Lett. 2007 Mar 29;9(7):1403-5. doi: 10.1021/ol070309o. Epub 2007 Mar 9.

Development of diastereoselective birch reduction-alkylation reactions of bi- and tricyclic beta-alkoxy-alpha,beta-unsaturated ketones.

J Org Chem. 2009 Sep 4;74(17):6623-30. doi: 10.1021/jo901094x.

Organic ligand-free alkylation of amines, carboxamides, sulfonamides, and ketones by using alcohols catalyzed by heterogeneous Ag/Mo oxides.

Chemistry. 2011 Jan 17;17(3):1021-8. doi: 10.1002/chem.201001915. Epub 2010 Nov 9.

Arylation and vinylation of alpha-diazocarbonyl compounds with boroxines.

Org Lett. 2009 Apr 2;11(7):1667-70. doi: 10.1021/ol900362d.

Tandem beta-alkylation-alpha-arylation of amines by carbolithiation and rearrangement of N-carbamoyl enamines (vinyl ureas).

J Am Chem Soc. 2010 May 19;132(19):6624-5. doi: 10.1021/ja1007992.

引用本文的文献

Diastereoselective Umpolung cyclisation of ketones promoted by hypervalent iodine.

Chem Sci. 2025 May 13. doi: 10.1039/d5sc01085c.

Computational and Experimental Studies on the α-Functionalization of Ketones Using Domino Reactions: A Strategy to Increase Chemoselectivity at the α-Carbon of Ketones.

Molecules. 2025 Feb 28;30(5):1114. doi: 10.3390/molecules30051114.

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Molecules. 2024 Jul 23;29(15):3454. doi: 10.3390/molecules29153454.

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Acc Chem Res. 2023 Jun 20;56(12):1634-1644. doi: 10.1021/acs.accounts.3c00171. Epub 2023 May 25.

Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination.

Org Lett. 2021 Mar 19;23(6):2094-2098. doi: 10.1021/acs.orglett.1c00251. Epub 2021 Feb 26.

α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation.

Angew Chem Int Ed Engl. 2020 Nov 16;59(47):20935-20939. doi: 10.1002/anie.202006398. Epub 2020 Sep 11.

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung.

Angew Chem Int Ed Engl. 2020 Oct 5;59(41):18208-18212. doi: 10.1002/anie.202007439. Epub 2020 Aug 17.

An umpolung strategy to react catalytic enols with nucleophiles.

Nat Commun. 2019 Nov 20;10(1):5244. doi: 10.1038/s41467-019-13175-5.

α-Arylation of Carbonyl Compounds through Oxidative C-C Bond Activation.

Angew Chem Int Ed Engl. 2019 Jul 15;58(29):9816-9819. doi: 10.1002/anie.201904899. Epub 2019 Jun 6.

Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.

J Am Chem Soc. 2017 Nov 15;139(45):16040-16043. doi: 10.1021/jacs.7b08813. Epub 2017 Nov 3.