Modular Synthesis of α,α-Diaryl α‑Amino Esters via Bi(V)-Mediated Arylation/SN2‑Displacement of Kukhtin–Ramirez Intermediates
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 SN2 displacement b...
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| Published in | Organic letters Vol. 24; no. 43; pp. 8002 - 8007 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
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American Chemical Society
04.11.2022
Amer Chemical Soc |
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| Abstract | 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 SN2 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. |
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| AbstractList | 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. We report a concise and modular approach to alpha,alpha- diaryl alpha-amino esters from readily available alpha-keto esters. This mild, one-pot protocol proceeds via ketone umpolung, with in situ formation of a Kukhtin-Ramirez intermediate preceding sequen-tial electrophilic arylation by Bi(V) and SN2 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 alpha-keto ester substrates. 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 SN2 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. |
| Author | Ball, Liam T. Denton, Ross M. Calcatelli, Alessio |
| AuthorAffiliation | GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry School of Chemistry |
| AuthorAffiliation_xml | – name: GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry – name: School of Chemistry |
| Author_xml | – sequence: 1 givenname: Alessio orcidid: 0000-0002-2571-5841 surname: Calcatelli fullname: Calcatelli, Alessio organization: School of Chemistry – sequence: 2 givenname: Ross M. orcidid: 0000-0003-1267-1971 surname: Denton fullname: Denton, Ross M. organization: GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry – sequence: 3 givenname: Liam T. orcidid: 0000-0003-3849-9006 surname: Ball fullname: Ball, Liam T. email: liam.ball@nottingham.ac.uk organization: School of Chemistry |
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| Keywords | CONFORMATIONAL BEHAVIOR PHOSPHORUS DESIGN ORGANOBISMUTH REAGENTS LIGANDS ACIDS ALKYL ARYL SULFIDES CATALYZED ASYMMETRIC ARYLATION CHEMISTRY TERTIARY |
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| Snippet | 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... We report a concise and modular approach to alpha,alpha- diaryl alpha-amino esters from readily available alpha-keto esters. This mild, one-pot protocol... 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... |
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| SubjectTerms | Chemistry Chemistry, Organic Letter Physical Sciences Science & Technology |
| Title | Modular Synthesis of α,α-Diaryl α‑Amino Esters via Bi(V)-Mediated Arylation/SN2‑Displacement of Kukhtin–Ramirez Intermediates |
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