Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/S N 2-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 formation of a Kukhtin-Ramirez intermediate preceding sequential electrophilic arylation by Bi(V) and S 2 displacement by an amin...

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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 United States 04.11.2022
Subjects
Amines
Amino Acids
Esters
Ketones
Molecular Structure
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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 formation of a Kukhtin-Ramirez intermediate preceding sequential electrophilic arylation by Bi(V) and S 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03201