Asymmetric synthesis of the two enantiomers of β-phosphorus-containing α-amino acids via hydrophosphinylation and hydrophosphonylation of chiral Ni(II)-complexes

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

doi:10.1039/D1QO00159K

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Asymmetric synthesis of the two enantiomers of β-phosphorus-containing α-amino acids via hydrophosphinylation and hydrophosphonylation of chiral Ni(ii)-complexes†

Yoshinori Tokairin,^a Hiroyuki Konno,

^b Angéline Noireau,^a Caroline West,

^a Hiroki Moriwaki,

^c Vadim A. Soloshonok,^de Cyril Nicolas

*^a and Isabelle Gillaizeau

*^a

Author affiliations

* Corresponding authors

^a Institute of Organic and Analytical Chemistry, ICOA UMR 7311 CNRS, Université d'Orléans, rue de Chartres, 45100 Orléans, France
E-mail: Isabelle.gillaizeau@univ-orleans.fr

^b Department of Biochemical Engineering, Graduate School of Science and Technology, Yamagata University, Yonezawa, Yamagata 992-8510, Japan

^c Hamari Chemicals Ltd., 1-19-40 Nankokita Suminoe-ku, Osaka 559-0034, Japan

^d Department of Organic Chemistry I, Faculty of Chemistry, University of Basque County UPV/EHU, Paseo Manuel Lardizabal 3, 20018 San Sebastian, Spain

^e IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza, Bizkaia, 48011 Bilbao, Spain

Abstract

A new approach for the asymmetric 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.

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Article information

DOI: https://doi.org/10.1039/D1QO00159K
Article type: Research Article
Submitted: 31 Jan 2021
Accepted: 25 Feb 2021
First published: 25 Feb 2021

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Org. Chem. Front., 2021,8, 2190-2195

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Asymmetric synthesis of the two enantiomers of β-phosphorus-containing α-amino acids via hydrophosphinylation and hydrophosphonylation of chiral Ni(II)-complexes

Y. Tokairin, H. Konno, A. Noireau, C. West, H. Moriwaki, V. A. Soloshonok, C. Nicolas and I. Gillaizeau, Org. Chem. Front., 2021, 8, 2190 DOI: 10.1039/D1QO00159K

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Organic Chemistry Frontiers

Asymmetric synthesis of the two enantiomers of β-phosphorus-containing α-amino acids via hydrophosphinylation and hydrophosphonylation of chiral Ni(ii)-complexes†

Abstract

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Asymmetric synthesis of the two enantiomers of β-phosphorus-containing α-amino acids via hydrophosphinylation and hydrophosphonylation of chiral Ni(II)-complexes

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