Literature DB >> 23715058

Chemical approach for interconversion of (S)- and (R)-α-amino acids.

Alexander E Sorochinsky1, Hisanori Ueki, José Luis Aceña, Trevor K Ellis, Hiroki Moriwaki, Tatsunori Sato, Vadim A Soloshonok.   

Abstract

Here we report a general method for the preparation of unnatural (R)-α-amino acids via complexation of α-(phenyl)ethylamine derived chiral reagent (S)- with various (S)-α-amino acids. The reactions proceed with synthetically useful chemical yields and thermodynamically controlled diastereoselectivity. Chiral reagent (S)- can be conveniently recovered and reused without any loss of enantiomeric purity and reactivity.

Entities:  

Mesh:

Substances:

Year:  2013        PMID: 23715058     DOI: 10.1039/c3ob40541a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  5 in total

1.  Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; a case of configurationally stable stereogenic nitrogen.

Authors:  Hiroki Moriwaki; Daniel Resch; Hengguang Li; Iwao Ojima; Ryosuke Takeda; José Luis Aceña; Vadim A Soloshonok
Journal:  Beilstein J Org Chem       Date:  2014-02-19       Impact factor: 2.883

2.  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 3.  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

4.  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

Review 5.  New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary.

Authors:  Marzena Wosińska-Hrydczuk; Jacek Skarżewski
Journal:  Molecules       Date:  2020-10-23       Impact factor: 4.411

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.