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

Autor: Dr. Yoshinori Tokairin, Yuhei Shigeno, Dr. Jianlin Han, Prof. Dr. Gerd‐Volker Röschenthaler, Dr. Hiroyuki Konno, Dr. Hiroki Moriwaki, Vadim A. Soloshonok

Publikováno v: ChemistryOpen, Vol 9, Iss 1, Pp 93-96 (2020)

Abstract Four differently substituted chiral Ni(II)‐complexes of dehydroalanine Schiff base were prepared and reacted with BrCF2COOEt/Cu under the standard reaction conditions. The observed diastereoselectivity was found to depend on the degree and

Externí odkaz: https://doaj.org/article/a14ab8c55028449498397b09fa6722bd

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

Autor: Hiroyuki Konno, Yoshinori Tokairin, Yuhei Shigeno, Gerd-Volker Röschenthaler, Jianlin Han, Hiroki Moriwaki, Vadim A. Soloshonok

Publikováno v: ChemistryOpen, Vol 9, Iss 1, Pp 93-96 (2020)
ChemistryOpen

Four differently substituted chiral Ni(II)‐complexes of dehydroalanine Schiff base were prepared and reacted with BrCF2COOEt/Cu under the standard reaction conditions. The observed diastereoselectivity was found to depend on the degree and pattern

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::13aa8f1ae919dd8c5d2cb805649857f1
https://doi.org/10.1002/open.201900343

Asymmetric synthesis of the two enantiomers of $\beta$-phosphorus-containing-$\alpha$-Amino Acids via hydrophosphinylation and hydrophosphonylation of chiral Ni(II)-complexes

Autor: Isabelle Gillaizeau, Angéline Noireau, Vadim A. Soloshonok, Hiroki Moriwaki, Hiroyuki Konno, Yoshinori Tokairin, Cyril Nicolas, Caroline West

Publikováno v: Organic Chemistry Frontiers
Organic Chemistry Frontiers, Royal Society of Chemistry, 2021, 8 (1-4), ⟨10.1039/D1QO00159K⟩
Organic Chemistry Frontiers, 2021, 8 (1-4), ⟨10.1039/D1QO00159K⟩

A new approach for the synthesis of the two enantiomers of β-phosphorus-containing α-amino acids was developed via Michael addition of secondary phosphine oxides and dialkyl phosphites to chiral Ni(ii)-complexes of a dehydroalanine-Schiff base.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ab70a439b127184b4048ec4129c1db2f
https://hal.archives-ouvertes.fr/hal-03359971/document

Preparation of (2 R , 3 R , 4 R )-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization

Autor: Hiroyuki Konno, Yoshinori Tokairin

Publikováno v: Tetrahedron. 73:39-45

Synthesis of a unique fatty acyl unit to build the N-terminus of callipeltin A and homophymine B is described. Our approach to access (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid uses enzymatic hydrolysis for the desymmetrization of achiral a

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::07a6424f2adf91ed1ebd1e31c1d3763e
https://doi.org/10.1016/j.tet.2016.11.050

Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling

Autor: Hiroyuki Konno, Yoshinori Tokairin, Vadim A. Soloshonok, Hiroki Moriwaki

Publikováno v: Amino acids. 51(3)

Practical new routes for preparation of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives, the key structural components of cytotoxic marine peptides callipeltin O and Q, suitable for the Fmoc-SPPS, were developed. (2S,3S)-Fmoc-3-Me-Gln(Xan)-

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8c97afd87c6224a8e511ec0a1f1848d5
https://pubmed.ncbi.nlm.nih.gov/30449004