Literature DB >> 28674862

Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes.

Yibing Wang1,2, Xiaohan Song1,2, Jiang Wang1,2, Hiroki Moriwaki3, Vadim A Soloshonok4,5, Hong Liu6,7.   

Abstract

This review article critically discusses examples of asymmetric synthesis of tailor-made α-amino acids via homologation of Ni(II) complexes of glycine and alanine Schiff bases, reported in the literature from 2013 through the end of 2016. Where it is possible, reaction mechanism and origin of the stereochemical outcome is discussed in detail. Special attention is given to various aspects of practicality and scalability of the reported methods. Among the most noticeable developments in this area are novel designs of axially chiral ligands, application of electro- and mechano-chemical (ball-milling) conditions, and development of dynamic kinetic resolution procedures.

Entities:  

Keywords:  Asymmetric synthesis; Ni(II) complexes; Practicality; Tailor-made amino acids; α-Amino acids

Mesh:

Substances:

Year:  2017        PMID: 28674862     DOI: 10.1007/s00726-017-2458-6

Source DB:  PubMed          Journal:  Amino Acids        ISSN: 0939-4451            Impact factor:   3.520


  9 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

Review 2.  Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids.

Authors:  Jianlin Han; Todd T Romoff; Hiroki Moriwaki; Hiroyuki Konno; Vadim A Soloshonok
Journal:  ACS Omega       Date:  2019-11-07

3.  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

4.  Enantioselective extraction of unprotected amino acids coupled with racemization.

Authors:  Haofei Huang; Yingji Jin; Mukesh E Shirbhate; Dayoung Kang; Misun Choi; Qian Chen; Youngmee Kim; Sung-Jin Kim; Il-Suk Byun; Ming Wang; Jean Bouffard; Seong Kyu Kim; Kwan Mook Kim
Journal:  Nat Commun       Date:  2021-01-05       Impact factor: 14.919

5.  Hexafluoroisobutylation of enolates through a tandem elimination/allylic shift/hydrofluorination reaction.

Authors:  Aline Delamare; Guillaume Naulet; Brice Kauffmann; Gilles Guichard; Guillaume Compain
Journal:  Chem Sci       Date:  2022-07-20       Impact factor: 9.969

Review 6.  The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine.

Authors:  Qian Wang; Jianlin Han; Alexander Sorochinsky; Aitor Landa; Greg Butler; Vadim A Soloshonok
Journal:  Pharmaceuticals (Basel)       Date:  2022-08-14

Review 7.  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

8.  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

9.  Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide.

Authors:  Silvia Vera; Ana Vázquez; Ricardo Rodriguez; Sandra Del Pozo; Iñaki Urruzuno; Abel de Cózar; Antonia Mielgo; Claudio Palomo
Journal:  J Org Chem       Date:  2021-05-16       Impact factor: 4.198

  9 in total

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