Literature DB >> 33504793

NiH-catalyzed asymmetric hydroarylation of N-acyl enamines to chiral benzylamines.

Yuli He1, Huayue Song1, Jian Chen1, Shaolin Zhu2.   

Abstract

Enantiomerically pure chiral amines and related amide derivatives are privilege motifs in many pharmacologically active molecules. In comparison to the well-established hydroamination, the transition metal-catalysed asymmetric hydrofunctionalization of enamines provides a complementary approach for their construction. Here we report a NiH-catalysed enantio- and regioselective reductive hydroarylation of N-acyl enamines, allowing for the practical access to a broad range of structurally diverse, enantioenriched benzylamines under mild, operationally simple reaction conditions.

Entities:  

Year:  2021        PMID: 33504793     DOI: 10.1038/s41467-020-20888-5

Source DB:  PubMed          Journal:  Nat Commun        ISSN: 2041-1723            Impact factor:   14.919


  39 in total

Review 1.  Transition metal-catalyzed enantioselective hydrogenation of enamines and imines.

Authors:  Jian-Hua Xie; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Rev       Date:  2010-12-17       Impact factor: 60.622

2.  Nickel Hydride Complexes.

Authors:  Nathan A Eberhardt; Hairong Guan
Journal:  Chem Rev       Date:  2016-07-20       Impact factor: 60.622

Review 3.  Direct catalytic asymmetric synthesis of α-chiral primary amines.

Authors:  Qin Yin; Yongjie Shi; Jingxin Wang; Xumu Zhang
Journal:  Chem Soc Rev       Date:  2020-07-15       Impact factor: 54.564

4.  Reductive Amination in the Synthesis of Pharmaceuticals.

Authors:  Oleg I Afanasyev; Ekaterina Kuchuk; Dmitry L Usanov; Denis Chusov
Journal:  Chem Rev       Date:  2019-10-21       Impact factor: 60.622

5.  New Strategies for the Transition-Metal Catalyzed Synthesis of Aliphatic Amines.

Authors:  Aaron Trowbridge; Scarlett M Walton; Matthew J Gaunt
Journal:  Chem Rev       Date:  2020-02-17       Impact factor: 60.622

6.  Branch-Selective Hydroarylation: Iodoarene-Olefin Cross-Coupling.

Authors:  Samantha A Green; Jeishla L M Matos; Akiko Yagi; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2016-09-21       Impact factor: 15.419

7.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

8.  Enantio- and regioselective CuH-catalyzed hydroamination of alkenes.

Authors:  Shaolin Zhu; Nootaree Niljianskul; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-10-15       Impact factor: 15.419

Review 9.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

10.  Practical carbon-carbon bond formation from olefins through nickel-catalyzed reductive olefin hydrocarbonation.

Authors:  Xi Lu; Bin Xiao; Zhenqi Zhang; Tianjun Gong; Wei Su; Jun Yi; Yao Fu; Lei Liu
Journal:  Nat Commun       Date:  2016-04-01       Impact factor: 14.919

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  8 in total

1.  Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides.

Authors:  Sii Hong Lau; Meredith A Borden; Talia J Steiman; Lucy S Wang; Marvin Parasram; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2021-09-20       Impact factor: 15.419

2.  Regio- and enantioselective remote hydroarylation using a ligand-relay strategy.

Authors:  Yuli He; Jiawei Ma; Huayue Song; Yao Zhang; Yong Liang; You Wang; Shaolin Zhu
Journal:  Nat Commun       Date:  2022-05-05       Impact factor: 17.694

3.  Allylic C-H amination cross-coupling furnishes tertiary amines by electrophilic metal catalysis.

Authors:  Brenna G Budaitis; Devon F A Fontaine; Siraj Z Ali; Andria L Pace; Jacob A Garwin; M Christina White
Journal:  Science       Date:  2022-04-14       Impact factor: 63.714

4.  Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations.

Authors:  Shan Wang; Jian-Xin Zhang; Tian-Yi Zhang; Huan Meng; Bi-Hong Chen; Wei Shu
Journal:  Nat Commun       Date:  2021-05-13       Impact factor: 14.919

5.  DFT insight into asymmetric alkyl-alkyl bond formation via nickel-catalysed enantioconvergent reductive coupling of racemic electrophiles with olefins.

Authors:  Chao-Shen Zhang; Bei-Bei Zhang; Liang Zhong; Xiang-Yu Chen; Zhi-Xiang Wang
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825

6.  Hydroarylation of enamides enabled by HFIP via a hexafluoroisopropyl ether as iminium reservoir.

Authors:  Nicolas Zeidan; Sergiu Bicic; Robert J Mayer; David Lebœuf; Joseph Moran
Journal:  Chem Sci       Date:  2022-06-27       Impact factor: 9.969

7.  Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates.

Authors:  Yao Zhang; Deyong Qiao; Mei Duan; You Wang; Shaolin Zhu
Journal:  Nat Commun       Date:  2022-09-26       Impact factor: 17.694

8.  Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes.

Authors:  Xiaoli Jiang; Bo Han; Yuhang Xue; Mei Duan; Zhuofan Gui; You Wang; Shaolin Zhu
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919

  8 in total

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