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Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/S_N2-Displacement of Kukhtin-Ramirez Intermediates.

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 S_N2 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.

SUBMITTER: Calcatelli A

PROVIDER: S-EPMC9641671 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin-Ramirez Intermediates.

Calcatelli Alessio A Denton Ross M RM Ball Liam T LT

Organic letters 20221024 43

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 ...[more]

PMID: 36278869

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