Enantioselective Cu‐Catalyzed Functionalizations of Unactivated Alkenes

Sorádová, Zuzana; Šebesta, Radovan

doi:10.1002/cctc.201600252

Cited by 40 publications

(10 citation statements)

References 71 publications

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“…Accordingly, substantial endeavors have been witnessed in developing new synthetic methods to access or utilize this class of compounds. [ 1‐7 ] Among the developed methods, transition metal‐catalyzed difunctionalization of alkenes enables preparation of complex molecules from simple available alkenes by diversifying the C=C double bond with high atom‐ and step‐economic efficiency. [ 8‐21 ] In particular, the dicarbofunctionalization of alkenes has gained special attention because it can construct complex carbon skeletons by assembling two carbon entities across the C=C bond and forming two C—C bonds in an one‐pot reaction (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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As a straightforward strategy for rapidly increasing molecular complexity, dicarbofunctionalization of alkenes has attracted substantial interests of organic synthesis, medicine chemistry, and materials science. Nickel-catalyzed cascade dicarbofunctionalizations have been flourished in this area recently, and nickel-mediated radical pathways particularly offer new opportunities in conjunctive cross-couplings with alkyl coupling partners. Herein, we give a comprehensive review of nickel-catalyzed dicarbofunctionalization of alkenes through a historical perspective, including intermolecular three-component reactions and intramolecular cascade reactions. Among the pathways discussed in this review, the carbometallation/cross-coupling process and the radical addition/cross-coupling process are the two major pathways for the nickel-catalyzed dicarbofunctionalization of alkenes. The oxidative cyclization and 1,2-metallate shift processes are also selectively discussed. These methods overcome the limitations associated with the reactions using noble metals in the field, providing an efficient and straightforward access to structurally diversified molecules. Yun-Cheng Luo (right) received his BSc degree in 2016 and master degree in 2019 from University of Science and Technology of China. Then he joined Professor Xingang Zhang's group at Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences to pursue his doctorate in organic chemistry. His research interests are focused on the activation of inert C-H or C-X bonds of bulky chemicals and their applications in the synthesis of fluorine-containing compounds. Chang Xu (middle) obtained his BSc degree in basic pharmacy from China Pharmaceutical University (China) in 2015. With an interest in organic chemistry and medicinal chemistry, he then began his graduate studies at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences under the supervision of Professor Xingang Zhang. His research interests are focused on the activation and transformations of fluoroalkylanes and their applications in medicinal chemistry. Xingang Zhang (left) obtained his BSc degree in 1998 from Sichuan University (China) and received the Ph.D. in 2003 at Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. After his postdoctoral work at University of Illinois at Urbana Champaign (USA), he joined the faculty team of SIOC as a research associate professor in 2008, and became research professor in 2012. His current research interests are focused on organofluorine chemistry and chemical biology.

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Section: Introductionmentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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“…Enantioselective insertion of alkenes into achiral metalÀ hydride bond represents ag eneral approach to access chiral metal-alkyl species. [13] Very recently,c hiral Cu-alkyl complexes,formed by migratory insertion of alkenes into achiral Cu À Hspecies, [14] have provided aplatform for awide range of asymmetric organic reactions and can readily react with various electrophiles,i ncluding hydroxylamine O-benzoylesters, [15] carbonyl compounds, [16] imines, [17] and allyl halides. [18] We envisioned that ac hiral Cu-alkyl species,g enerated by insertion of alkenes into achiral Cu À Hspecies,could react with quinoline N-oxides to produce chiral 2-alkylated quinolines (Scheme 1D).…”

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Enantioselective Copper‐Catalyzed Alkylation of Quinoline N‐Oxides with Vinylarenes

Sang

2017

Angew Chem Int Ed

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An asymmetric copper‐catalyzed alkylation of quinoline N‐oxides with chiral Cu–alkyl species, generated by migratory insertion of a vinylarene into a chiral Cu−H complex, is reported. A variety of quinoline N‐oxides and vinylarenes underwent this Cu‐catalyzed enantioselective alkylation reaction, affording the corresponding chiral alkylated N‐heteroarenes in high yield with high‐to‐excellent enantioselectivity. This enantioselective protocol represents the first general and practical approach to access a wide range of chiral alkylated quinolines.

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“…CuH-catalyzed Page 4 of 21 CCS Chemistry enantioselective hydroamination of alkenes, pioneered by Buchwald, Hirano and Miura in 2013, [52][53] is one of the most powerful tools for the preparation of chiral amine derivatives. [54][55][56][57][58][59][60][61][62][63][64] Recently, Buchwald developed a reversal Cu-catalyzed enantioselective hydroamination of α, β-unsaturated carbonyl compounds with 1,2benzisoxazole which readily gives primary amines. 65 Simultaneously, Zhang reported a similar reversal hydroamination, capable of directly producing a series of β-amino acids, esters, amides and nitriles.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Access of γ-Amino Acids and γ-Amino Phosphonic Acid Derivatives via Copper-Catalyzed Enantioselective and Regioselective Hydroamination

Yang

Jiang

et al. 2022

CCS Chem

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γ-Aminobutyric acid is a major inhibitory neurotransmitter in the mammalian central nervous system that plays a substantial role in brain disorders. γ-Amino phosphonic acid is an unique surrogate of both natural and unnatural γ-amino acid. Because of their unique biological activity, γ-Amino acid, as well as γ-amino phosphonic acid derivatives have attracted considerable attentions. However, efficient and straightforward method for constructing chiral γ-substituted-γ-amino acid and γ-amino phosphonic acid derivatives remains a longstanding challenge. Herein, a highly efficient, versatile and universal Cu-catalyzed asymmetric hydroamination of cinnamyl esters, cinnamyl phosphonates and cinnamyl phosphine oxides is presented for accessing γ-amino acid and γ-amino phosphonic acid derivatives in good yields with high level of enantiocontrollings and regioselectivities.

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Enantioselective Cu‐Catalyzed Functionalizations of Unactivated Alkenes

Cited by 40 publications

References 71 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Enantioselective Copper‐Catalyzed Alkylation of Quinoline N‐Oxides with Vinylarenes

Asymmetric Access of γ-Amino Acids and γ-Amino Phosphonic Acid Derivatives via Copper-Catalyzed Enantioselective and Regioselective Hydroamination

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Enantioselective Cu‐Catalyzed Functionalizations of Unactivated Alkenes

Cited by 40 publications

References 71 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Enantioselective Copper‐Catalyzed Alkylation of Quinoline N‐Oxides with Vinylarenes

Asymmetric Access of γ-Amino Acids and γ-Amino Phosphonic Acid Derivatives via Copper-Catalyzed Enantioselective and Regioselective Hydroamination

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Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†