Pd‐Catalyzed δ‐C(sp3)−H Thiolation of Amino Acid Derivatives

Author:

García‐Viada Andrés1,Sánchez‐González Celia1,Martínez‐Mingo Mario2,Alonso Inés13,Rodríguez Nuria13ORCID,Carretero Juan C.13

Affiliation:

1. Dpto. de Química Orgánica Facultad de Ciencias Universidad Autónoma de Madrid (UAM) Cantoblanco 28049 Madrid Spain

2. Instituto Madrileño de Estudios Avanzados en Nanociencia (IMDEA-Nanociencia) 28049 Madrid Spain

3. Institute for Advanced Research in Chemical Sciences (IAdChem) and Center for Innovation in Advanced Chemistry (ORFEO-CINQA) UAM 28049 Madrid Spain

Abstract

AbstractHerein, we report a protocol for the selective δ‐thiolation of aliphatic α‐amino acids catalyzed by a Pd(II)/Ag(I) system. This reaction employs disulfides as thiolating agents and N‐COPy as directing group, providing valuable non‐proteinogenic amino acid derivatives in moderate to good diastereoselectivities and yields. Remarkably, the method is also suitable for the late‐stage functionalization of a dipeptide. Experimental and DFT studies have provided significant insights into the mechanism and underlying factors controlling the selectivity of the process and determining the key role of the silver salt.

Publisher

Wiley

Subject

General Chemistry

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