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

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posted on 2022-10-24, 12:09 authored by Alessio Calcatelli, Ross M. Denton, Liam T. Ball
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.