Organic Chemistry Portal



Synthesis of Silacyclic Dipeptides: Peptide Elongation at Both N- and C-Termini of Dipeptide

Tomohiro Hattori* and Hisashi Yamamoto*

*Peptide Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan, Email:,

T. Hattori, H. Yamamoto, J. Am. Chem. Soc., 2022, 144, 1758-1765.

DOI: 10.1021/jacs.1c11260

see article for more reactions


Imidazolylsilanes are highly useful coupling reagents for peptide synthesis from N-,C-terminal unprotected amino acids with amino acid tert-butyl esters. An optional deprotection of the tert-butyl ester at the C-terminus and cyclization sequentially proceed to afford silacyclic dipeptides, that can act as both nucleophiles and electrophiles for further peptide elongation.

see article for more examples

Oligopeptide Synthesis

Organocatalytic Activation of Inert Hydrosilane for Peptide Bond Formation

W. Muramatsu, H. Yamamoto, Org. Lett., 2022, 24, 7194-7199.

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: J48-Y2022