Literature DB >> 27023199

Enantioselective Intermolecular Enamide-Aldehyde Cross-Coupling Catalyzed by Chiral N-Heterocyclic Carbenes.

Jicheng Wu1, Changgui Zhao1, Jian Wang1.   

Abstract

The unprecedented N-heterocyclic carbene (NHC)-catalyzed intermolecular cross-coupling of enamides and aldehydes is described. Upon exposure of enamides to aldehydes in the presence of a NHC catalyst, catalytic C-C bond formation occurs, providing highly enantioselective N-protected amines, bearing a quaternary carbon center, in good yields and with high enantioselectivities.

Entities:  

Year:  2016        PMID： 27023199     DOI： 10.1021/jacs.5b13501

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  5 in total

1.  Insights into the Competing Mechanisms and Origin of Enantioselectivity for N-Heterocyclic Carbene-Catalyzed Reaction of Aldehyde with Enamide.

Authors:  Yan Qiao; Xinhuan Chen; Donghui Wei; Junbiao Chang
Journal:  Sci Rep       Date:  2016-12-01       Impact factor: 4.379

2.  PEG 400/Cerium Ammonium Nitrate Combined with Microwave-Assisted Synthesis for Rapid Access to Beta-Amino Ketones. An Easy-to-Use Protocol for Discovering New Hit Compounds.

Authors:  Giacomo Rossino; Maria Valeria Raimondi; Marta Rui; Marcello Di Giacomo; Daniela Rossi; Simona Collina
Journal:  Molecules       Date:  2018-03-28       Impact factor: 4.411

3.  The Role of the Fused Ring in Bicyclic Triazolium Organocatalysts: Kinetic, X-ray, and DFT Insights.

Authors:  Jiayun Zhu; Inmaculada Moreno; Peter Quinn; Dmitry S Yufit; Lijuan Song; Claire M Young; Zhuan Duan; Andrew R Tyler; Paul G Waddell; Michael J Hall; Michael R Probert; Andrew D Smith; AnnMarie C O'Donoghue
Journal:  J Org Chem       Date:  2022-03-01       Impact factor: 4.354

4.  Enantioselective synthesis of α-amino ketones through palladium-catalyzed asymmetric arylation of α-keto imines.

Authors:  Wei Wen; Zhao-Pin Ai; Chang-Lin Yang; Chao-Xing Li; Zhu-Lian Wu; Tian Cai; Qi-Xiang Guo
Journal:  Chem Sci       Date:  2022-03-07       Impact factor: 9.825

5.  Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis.

Authors:  Zhouli Hu; Chenlong Wei; Qianqian Shi; Xianfang Hong; Jinhua Liu; Xiangui Zhou; Jinna Han; Wei Cao; Ashis Kumar Gupta; Xiaoxiang Zhang; Donghui Wei; Zhenqian Fu; Wei Huang
Journal:  Nat Commun       Date:  2022-07-13       Impact factor: 17.694
  5 in total

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