Selective quantitative N-functionalization of unprotected α-amino acids using NHC-Ir(III) catalyst

Beatriz Saavedra; Aitor Bermejo-López; Majken Raeder; Belén Martín-Matute

doi:10.1016/j.xpro.2023.102147

Selective quantitative N-functionalization of unprotected α-amino acids using NHC-Ir(III) catalyst

STAR Protoc. 2023 Mar 13;4(2):102147. doi: 10.1016/j.xpro.2023.102147. Online ahead of print.

Authors

Beatriz Saavedra¹, Aitor Bermejo-López¹, Majken Raeder¹, Belén Martín-Matute²

Affiliations

¹ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
² Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden. Electronic address: belen.martin.matute@su.se.

Abstract

Unnatural amino acids are valuable building blocks with numerous applications. Here, we present a quantitative technique for accessing mono-N-functionalized amino acids directly from unprotected substrates using alcohols as alkylating agents and an NHC-Ir(III) catalyst. We detail specific steps for catalyst preparation and application, as well as for catalyst recycling. The protocol excludes a few amino acids (l-cysteine, l-lysine, and l-arginine) and secondary alcohols. For complete details on the use and execution of this protocol, please refer to Bermejo-López et al. (2022).¹.

Keywords: Chemistry; Environmental Sciences.