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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Bibliographic Details
Published inOrganic letters Vol. 24; no. 43; pp. 8002 - 8007
Main Authors Calcatelli, Alessio, Denton, Ross M., Ball, Liam T.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
CONFORMATIONAL BEHAVIOR
PHOSPHORUS
DESIGN
ORGANOBISMUTH REAGENTS
LIGANDS
ACIDS
ALKYL ARYL SULFIDES
CATALYZED ASYMMETRIC ARYLATION
CHEMISTRY
TERTIARY
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03201