Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

A variety of chiral N-phosphinyl α-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected α-amino esters. The reduction proceeded very well with excellent chemical yields (88–...

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Detalles Bibliográficos
Autores principales: Xiong, Yiwen, Mei, Haibo, Wu, Lingmin, Han, Jianlin, Pan, Yi, Li, Guigen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999852/
https://www.ncbi.nlm.nih.gov/pubmed/24778716
http://dx.doi.org/10.3762/bjoc.10.57
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author Xiong, Yiwen
Mei, Haibo
Wu, Lingmin
Han, Jianlin
Pan, Yi
Li, Guigen
author_facet Xiong, Yiwen
Mei, Haibo
Wu, Lingmin
Han, Jianlin
Pan, Yi
Li, Guigen
author_sort Xiong, Yiwen
collection PubMed
description A variety of chiral N-phosphinyl α-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected α-amino esters. The reduction proceeded very well with excellent chemical yields (88–98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.
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spelling pubmed-39998522014-04-28 Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction Xiong, Yiwen Mei, Haibo Wu, Lingmin Han, Jianlin Pan, Yi Li, Guigen Beilstein J Org Chem Full Research Paper A variety of chiral N-phosphinyl α-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected α-amino esters. The reduction proceeded very well with excellent chemical yields (88–98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions. Beilstein-Institut 2014-03-13 /pmc/articles/PMC3999852/ /pubmed/24778716 http://dx.doi.org/10.3762/bjoc.10.57 Text en Copyright © 2014, Xiong et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Xiong, Yiwen
Mei, Haibo
Wu, Lingmin
Han, Jianlin
Pan, Yi
Li, Guigen
Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
title Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
title_full Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
title_fullStr Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
title_full_unstemmed Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
title_short Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
title_sort synthesis of chiral n-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999852/
https://www.ncbi.nlm.nih.gov/pubmed/24778716
http://dx.doi.org/10.3762/bjoc.10.57
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