Organocatalytic Activation of Inert Hydrosilane for Peptide Bond Formation
Wataru Muramatsu* and Hisashi Yamamoto*
*Peptide Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan,
Email: muramatsu
isc.chubu.ac.jp, hyamamotoisc.chubu.ac.jp
W. Muramatsu, H. Yamamoto, Org. Lett., 2022, 24, 7194-7199.
DOI: 10.1021/acs.orglett.2c02947
Abstract
HSi[OCH(CF3)2]3 catalyzes a reliable protocol for peptide bond formation in high yield that is generally applicable to natural and unnatural α-amino acids, β-amino acids, and peptides bearing various functional groups. This method facilitates the sustainable utilization of natural resources by using a catalyst and an auxiliary based on earth-abundant silicon.
see article for more examples
proposed mechanism
Synthesis of Silacyclic Dipeptides: Peptide Elongation at Both N- and C-Termini of Dipeptide
T. Hattori, H. Yamamoto, J. Am. Chem. Soc., 2022, 144, 1758-1765.
Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents
W. Muramatsu, H. Yamamoto, J. Am. Chem. Soc., 2021, 143, 6792-6797.
Tantalum-Catalyzed Amidation of Amino Acid Homologues
W. Muramatsu, H. Yamamoto, J. Am. Chem. Soc., 2019, 141, 18926-18931.
Key Words
ID: J54-Y2022
