Literature DB >> 33775097

Recent Advances in Catalytic Asymmetric Construction of Atropisomers.

Jun Kee Cheng1, Shao-Hua Xiang1,2, Shaoyu Li1,2, Liu Ye1,2, Bin Tan1.   

Abstract

Atropisomerism is a stereochemical behavior portrayed by three-dimensional molecules that bear rotationally restricted σ bond. Akin to the well-represented point-chiral molecules, atropisomerically chiral compounds are finding increasing utilities in many disciplines where molecular asymmetry is influential. This provides steady demand on atroposelective synthesis, where numerous synthetic pursuits have been rewarded with conceptually novel and streamlined methods while expanding the structural diversity of atropisomers. This review summarizes key achievements in stereoselective preparation of biaryl, heterobiaryl, and nonbiaryl atropisomers documented between 2015 and 2020. Emphasis is placed on the synthetic strategies for each structural class, while examples are cited to illustrate the potential applications of the accessed atropochiral targets.

Entities:  

Year:  2021        PMID: 33775097     DOI: 10.1021/acs.chemrev.0c01306

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  23 in total

1.  Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation.

Authors:  Hyung Yoon; Alexandra Galls; Soren D Rozema; Scott J Miller
Journal:  Org Lett       Date:  2022-01-10       Impact factor: 6.005

2.  Counterion-Mediated Enantioconvergent Synthesis of Axially Chiral Medium Rings.

Authors:  Ji-Yuan Du; Tudor Balan; Tim D W Claridge; Martin D Smith
Journal:  J Am Chem Soc       Date:  2022-08-03       Impact factor: 16.383

Review 3.  Addressing Atropisomerism in the Development of Sotorasib, a Covalent Inhibitor of KRAS G12C: Structural, Analytical, and Synthetic Considerations.

Authors:  Brian A Lanman; Andrew T Parsons; Stephan G Zech
Journal:  Acc Chem Res       Date:  2022-09-30       Impact factor: 24.466

4.  Catalytic Atroposelective C7 Functionalisation of Indolines and Indoles.

Authors:  Saad Shaaban; Christian Merten; Herbert Waldmann
Journal:  Chemistry       Date:  2021-11-05       Impact factor: 5.020

5.  Catalytic atroposelective synthesis of axially chiral benzonitriles via chirality control during bond dissociation and CN group formation.

Authors:  Ya Lv; Guoyong Luo; Qian Liu; Zhichao Jin; Xinglong Zhang; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2022-01-10       Impact factor: 17.694

6.  Carbene-catalyzed atroposelective synthesis of axially chiral styrenes.

Authors:  Jia-Lei Yan; Rakesh Maiti; Shi-Chao Ren; Weiyi Tian; Tingting Li; Jun Xu; Bivas Mondal; Zhichao Jin; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2022-01-10       Impact factor: 14.919

7.  Asymmetric synthesis of dibenzo[b,d]azepines by Cu-catalyzed reductive or borylative cyclization.

Authors:  Patricia Rodríguez-Salamanca; Rocío Martín-de la Calle; Verónica Rodríguez; Pedro Merino; Rosario Fernández; José M Lassaletta; Valentín Hornillos
Journal:  Chem Sci       Date:  2021-11-10       Impact factor: 9.825

8.  Asymmetric synthesis of N-N axially chiral compounds via organocatalytic atroposelective N-acylation.

Authors:  Wei Lin; Qun Zhao; Yao Li; Ming Pan; Chen Yang; Guo-Hui Yang; Xin Li
Journal:  Chem Sci       Date:  2021-11-24       Impact factor: 9.825

9.  Brønsted acid-enhanced copper-catalyzed atroposelective cycloisomerization to axially chiral arylquinolizones via dearomatization of pyridine.

Authors:  Xiao-Long Min; Xiu-Lian Zhang; Wenbin Yi; Ying He
Journal:  Nat Commun       Date:  2022-01-18       Impact factor: 17.694

10.  Cu(i) catalysis for selective condensation/bicycloaromatization of two different arylalkynes: direct and general construction of functionalized C-N axial biaryl compounds.

Authors:  Qian Shang; Haifang Tang; Yongping Liu; MingMing Yin; Lebin Su; Shimin Xie; Lixin Liu; Wen Yang; Yi Chen; Jianyu Dong; Yongbo Zhou; Shuang-Feng Yin
Journal:  Chem Sci       Date:  2021-12-13       Impact factor: 9.825

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