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

Calcatelli, Alessio; Denton, Ross M.; Ball, Liam T.

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.

Citation

Calcatelli, A., Denton, R. M., & Ball, L. T. (2022). Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin–Ramirez Intermediates. Organic Letters, https://doi.org/10.1021/acs.orglett.2c03201

• Journal Article Type: Article
• Acceptance Date: Oct 13, 2022
• Online Publication Date: Oct 24, 2022
• Publication Date: Oct 24, 2022
• Deposit Date: Oct 27, 2022
• Publicly Available Date: Nov 2, 2022
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society (ACS)
• Peer Reviewed: Peer Reviewed
• DOI: https://doi.org/10.1021/acs.orglett.2c03201
• Keywords: Organic Chemistry, Physical and Theoretical Chemistry, Biochemistry
• Public URL: https://nottingham-repository.worktribe.com/output/12898503
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.orglett.2c03201