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Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement of Kukhtin–Ramirez Intermediates
[Image: see text] We report a concise and modular approach to α,α-diaryl α-amino esters from readily available α-keto esters. This mild, one-pot protocol proceeds via ketone umpolung, with in situ formation of a Kukhtin–Ramirez intermediate preceding sequential electrophilic arylation by Bi(V) and S...
| Autores principales: | , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2022
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641671/ https://www.ncbi.nlm.nih.gov/pubmed/36278869 http://dx.doi.org/10.1021/acs.orglett.2c03201 |
| _version_ | 1784826131156828160 |
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| author | Calcatelli, Alessio Denton, Ross M. Ball, Liam T. |
| author_facet | Calcatelli, Alessio Denton, Ross M. Ball, Liam T. |
| author_sort | Calcatelli, Alessio |
| collection | PubMed |
| description | [Image: see text] We report a concise and modular approach to α,α-diaryl α-amino esters from readily available α-keto esters. This mild, one-pot protocol proceeds via ketone umpolung, with in situ formation of a Kukhtin–Ramirez intermediate preceding sequential electrophilic arylation by Bi(V) and S(N)2 displacement by an amine. The methodology is compatible with a wide range of anilines and primary amines - including derivatives of drugs and proteinogenic amino acids - Bi(V) arylating agents, and α-keto ester substrates. |
| format | Online Article Text |
| id | pubmed-9641671 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-96416712022-11-15 Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement of Kukhtin–Ramirez Intermediates Calcatelli, Alessio Denton, Ross M. Ball, Liam T. Org Lett [Image: see text] We report a concise and modular approach to α,α-diaryl α-amino esters from readily available α-keto esters. This mild, one-pot protocol proceeds via ketone umpolung, with in situ formation of a Kukhtin–Ramirez intermediate preceding sequential electrophilic arylation by Bi(V) and S(N)2 displacement by an amine. The methodology is compatible with a wide range of anilines and primary amines - including derivatives of drugs and proteinogenic amino acids - Bi(V) arylating agents, and α-keto ester substrates. American Chemical Society 2022-10-24 2022-11-04 /pmc/articles/PMC9641671/ /pubmed/36278869 http://dx.doi.org/10.1021/acs.orglett.2c03201 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Calcatelli, Alessio Denton, Ross M. Ball, Liam T. Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement of Kukhtin–Ramirez Intermediates |
| title | Modular Synthesis
of α,α-Diaryl α-Amino
Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement
of Kukhtin–Ramirez Intermediates |
| title_full | Modular Synthesis
of α,α-Diaryl α-Amino
Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement
of Kukhtin–Ramirez Intermediates |
| title_fullStr | Modular Synthesis
of α,α-Diaryl α-Amino
Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement
of Kukhtin–Ramirez Intermediates |
| title_full_unstemmed | Modular Synthesis
of α,α-Diaryl α-Amino
Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement
of Kukhtin–Ramirez Intermediates |
| title_short | Modular Synthesis
of α,α-Diaryl α-Amino
Esters via Bi(V)-Mediated Arylation/S(N)2-Displacement
of Kukhtin–Ramirez Intermediates |
| title_sort | modular synthesis
of α,α-diaryl α-amino
esters via bi(v)-mediated arylation/s(n)2-displacement
of kukhtin–ramirez intermediates |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641671/ https://www.ncbi.nlm.nih.gov/pubmed/36278869 http://dx.doi.org/10.1021/acs.orglett.2c03201 |
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