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Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist
The chiral catalytic amination of an α,α-dialkyl substituted aldehyde usually proceeds with low enantioselectivity. We selected naphthyl-l-alanine as the catalyst and observed improved enantioselectivity for the amination. Using this method, racemic α-methyl-α-benzyloxypropanal was aminated to give...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073532/ https://www.ncbi.nlm.nih.gov/pubmed/35529148 http://dx.doi.org/10.1039/c9ra06210f |
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author | Xiao, Qiong Tang, Yifan Xie, Ping Yin, Dali |
author_facet | Xiao, Qiong Tang, Yifan Xie, Ping Yin, Dali |
author_sort | Xiao, Qiong |
collection | PubMed |
description | The chiral catalytic amination of an α,α-dialkyl substituted aldehyde usually proceeds with low enantioselectivity. We selected naphthyl-l-alanine as the catalyst and observed improved enantioselectivity for the amination. Using this method, racemic α-methyl-α-benzyloxypropanal was aminated to give chiral serine derivatives in 74% ee, which was further increased to >99% ee after recrystallization. Moreover, we also successfully synthesized a chiral phosphonium salt 9 for the preparation of one α-substituted alaninol compound 14 as an S1P(1) agonist in high overall yield. |
format | Online Article Text |
id | pubmed-9073532 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90735322022-05-06 Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist Xiao, Qiong Tang, Yifan Xie, Ping Yin, Dali RSC Adv Chemistry The chiral catalytic amination of an α,α-dialkyl substituted aldehyde usually proceeds with low enantioselectivity. We selected naphthyl-l-alanine as the catalyst and observed improved enantioselectivity for the amination. Using this method, racemic α-methyl-α-benzyloxypropanal was aminated to give chiral serine derivatives in 74% ee, which was further increased to >99% ee after recrystallization. Moreover, we also successfully synthesized a chiral phosphonium salt 9 for the preparation of one α-substituted alaninol compound 14 as an S1P(1) agonist in high overall yield. The Royal Society of Chemistry 2019-10-18 /pmc/articles/PMC9073532/ /pubmed/35529148 http://dx.doi.org/10.1039/c9ra06210f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Xiao, Qiong Tang, Yifan Xie, Ping Yin, Dali Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist |
title | Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist |
title_full | Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist |
title_fullStr | Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist |
title_full_unstemmed | Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist |
title_short | Asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a S1P(1) agonist |
title_sort | asymmetric amination of α,α-dialkyl substituted aldehydes catalyzed by a simple chiral primary amino acid and its application to the preparation of a s1p(1) agonist |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073532/ https://www.ncbi.nlm.nih.gov/pubmed/35529148 http://dx.doi.org/10.1039/c9ra06210f |
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