Literature DB >> 31117580

Catalytic Enantioselective Synthesis of N-C Axially Chiral Sulfonamides through Chiral Palladium-Catalyzed N-Allylation.

Yuki Kikuchi1, Chisato Nakamura1, Mizuki Matsuoka1, Rina Asami1, Osamu Kitagawa1.   

Abstract

In the presence of ( S,S)-Trost ligand and (allyl-Pd-Cl)2 catalyst, the reaction of allyl acetate with the anionic species prepared from various N-(2- tert-butylphenyl)sulfonamides and NaH proceeded in an enantioselective manner (up to 95% ee) to give optically active N-allylated sulfonamide derivatives possessing an N-C axially chiral structure in high yields.

Entities:  

Year:  2019        PMID: 31117580     DOI: 10.1021/acs.joc.9b00989

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Atropoenantioselective palladaelectro-catalyzed anilide C-H olefinations viable with natural sunlight as sustainable power source.

Authors:  Johanna Frey; Xiaoyan Hou; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

Review 2.  Asymmetric Synthesis of Axially Chiral C-N Atropisomers.

Authors:  Patricia Rodríguez-Salamanca; Rosario Fernández; Valentín Hornillos; José M Lassaletta
Journal:  Chemistry       Date:  2022-03-25       Impact factor: 5.020

Review 3.  Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C-N Axis via Enantioselective Catalysis.

Authors:  Xiao Xiao; Biao Chen; Yi-Ping Yao; Hai-Jie Zhou; Xu Wang; Neng-Zhong Wang; Fen-Er Chen
Journal:  Molecules       Date:  2022-10-04       Impact factor: 4.927

4.  Asymmetric allylic substitution-isomerization to axially chiral enamides via hydrogen-bonding assisted central-to-axial chirality transfer.

Authors:  Chao Sun; Xiaotian Qi; Xiao-Long Min; Xue-Dan Bai; Peng Liu; Ying He
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

  4 in total

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