Literature DB >> 15771484

Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction.

Osamu Kitagawa1, Masashi Takahashi, Masatoshi Yoshikawa, Takeo Taguchi.   

Abstract

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation of ortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89-95% ee) to give optically active atropisomeric anilides possessing N-C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94-96% ee).

Entities:  

Year:  2005        PMID： 15771484     DOI： 10.1021/ja042216x

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


  9 in total

1.  Direct amination of γ-halo-β-ketoesters with anilines.

Authors:  Yinan Zhang; Richard B Silverman
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

2.  Atropisomerism in the Pharmaceutically Relevant Realm.

Authors:  Mariami Basilaia; Matthew H Chen; Jim Secka; Jeffrey L Gustafson
Journal:  Acc Chem Res       Date:  2022-09-26       Impact factor: 24.466

3.  Rotational isomers of N-methyl-N-arylacetamides and their derived enolates: implications for asymmetric Hartwig oxindole cyclizations.

Authors:  Jérémie Mandel; Xiaohong Pan; E Ben Hay; Steven J Geib; Craig S Wilcox; Dennis P Curran
Journal:  J Org Chem       Date:  2013-04-09       Impact factor: 4.354

4.  A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

Authors:  Jossian Oppenheimer; Whitney L Johnson; Ruth Figueroa; Ryuji Hayashi; Richard P Hsung
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

5.  Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination.

Authors:  He-Yuan Bai; Fu-Xin Tan; Tuan-Qing Liu; Guo-Dong Zhu; Jin-Miao Tian; Tong-Mei Ding; Zhi-Min Chen; Shu-Yu Zhang
Journal:  Nat Commun       Date:  2019-07-11       Impact factor: 14.919

6.  Palladium-catalyzed intramolecular C-H arylation of 2-halo-N-Boc-N-arylbenzamides for the synthesis of N-H phenanthridinones.

Authors:  Quan-Fang Hu; Tian-Tao Gao; Yao-Jie Shi; Qian Lei; Luo-Ting Yu
Journal:  RSC Adv       Date:  2018-04-13       Impact factor: 4.036

7.  Intermolecular Halogen Bond Detected in Racemic and Optically Pure N-C Axially Chiral 3-(2-Halophenyl)quinazoline-4-thione Derivatives.

Authors:  Ryosuke Matsui; Erina Niijima; Tomomi Imai; Hiroyuki Kobayashi; Akiko Hori; Azusa Sato; Yuko Nakamura; Osamu Kitagawa
Journal:  Molecules       Date:  2022-04-06       Impact factor: 4.411

Review 8.  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 9.  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
  9 in total

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