Literature DB >> 26367134

Recyclable Ligands for the Non-Enzymatic Dynamic Kinetic Resolution of Challenging α-Amino Acids.

Yong Nian1,2, Jiang Wang2, Shengbin Zhou2, Shuni Wang2, Hiroki Moriwaki3, Aki Kawashima3, Vadim A Soloshonok4,5, Hong Liu6,7.   

Abstract

Structurally simple and inexpensive chiral tridentate ligands were employed for substantially advancing the purely chemical dynamic kinetic resolution (DKR) of unprotected racemic tailor-made α-amino acids (TM-α-AAs), enabling the first DKR of TM-α-AAs bearing tertiary alkyl chains as well as multiple unprotected functional groups. Owing to the operationally convenient conditions, virtually complete stereoselectivity, and full recyclability of the source of chirality, this method should find wide applications for the preparation of TM-α-AAs, especially on large scale.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N ligands; amino acids; enantioselectivity; kinetic resolution; nickel

Mesh:

Substances:

Year:  2015        PMID: 26367134     DOI: 10.1002/anie.201507273

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

1.  Large-Scale Asymmetric Synthesis of Fmoc-(S)-2-Amino-6,6,6-Trifluorohexanoic Acid.

Authors:  Zizhen Yin; Hiroki Moriwaki; Hidenori Abe; Toshio Miwa; Jianlin Han; Vadim A Soloshonok
Journal:  ChemistryOpen       Date:  2019-06-07       Impact factor: 2.911

2.  Recyclable and Stable α-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free C,N-Unprotected α-Amino Acids.

Authors:  Shuangjie Shu; Liang Zhao; Shengbin Zhou; Chenglin Wu; Hong Liu; Jiang Wang
Journal:  Molecules       Date:  2019-06-13       Impact factor: 4.411

3.  A Convergent Total Synthesis of the Death Cap Toxin α-Amanitin.

Authors:  Mary-Ann J Siegert; Caroline H Knittel; Roderich D Süssmuth
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-06       Impact factor: 15.336

4.  Asymmetric Synthesis of 4,4-(Difluoro)glutamic Acid via Chiral Ni(II)-Complexes of Dehydroalanine Schiff Bases. Effect of the Chiral Ligands Structure on the Stereochemical Outcome.

Authors:  Yoshinori Tokairin; Yuhei Shigeno; Jianlin Han; Gerd-Volker Röschenthaler; Hiroyuki Konno; Hiroki Moriwaki; Vadim A Soloshonok
Journal:  ChemistryOpen       Date:  2020-01-29       Impact factor: 2.911

Review 5.  Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature.

Authors:  Yupiao Zou; Jianlin Han; Ashot S Saghyan; Anna F Mkrtchyan; Hiroyuki Konno; Hiroki Moriwaki; Kunisuke Izawa; Vadim A Soloshonok
Journal:  Molecules       Date:  2020-06-12       Impact factor: 4.411

6.  Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid.

Authors:  Jianlin Han; Ryosuke Takeda; Xinyi Liu; Hiroyuki Konno; Hidenori Abe; Takahiro Hiramatsu; Hiroki Moriwaki; Vadim A Soloshonok
Journal:  Molecules       Date:  2019-12-10       Impact factor: 4.411

  6 in total

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