Premium
Site‐Selective Cu‐Catalyzed Alkylation of α‐Amino Acids and Peptides toward the Assembly of Quaternary Centers
Author(s) -
San Segundo Marcos,
Correa Arkaitz
Publication year - 2018
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201802216
Subject(s) - chemoselectivity , alkylation , glycine , chemistry , amino acid , catalysis , chirality (physics) , alkyl , peptide , combinatorial chemistry , stereoisomerism , protein quaternary structure , aryl , stereochemistry , natural product , organic chemistry , biochemistry , protein subunit , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , gene , quark
The Cu I ‐catalyzed selective α‐alkylation of α‐amino acid and peptide derivatives with 2‐alkyl‐1,3‐dioxolanes is reported. This oxidative coupling is distinguished by its site‐specificity, high diastereoselectivity, and chirality preservation and exhibits absolute chemoselectivity for N ‐aryl glycine motifs over other amino acid units. Collectively, the method allows for the assembly of challenging quaternary centers, as well as compounds derived from natural products of high structural complexity, which may provide ample opportunities for late‐stage functionalization of peptides.