One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams

Abstract α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam rin...

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Veröffentlicht in:Synthesis (Stuttgart) 2020-12, Vol.52 (23), p.3657-3666
Hauptverfasser: Tarui, Atsushi, Ueo, Masakazu, Morikawa, Marino, Tsuta, Masahiko, Iwasaki, Sumika, Morishita, Noriko, Karuo, Yukiko, Sato, Kazuyuki, Kawai, Kentaro, Omote, Masaaki
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Sprache:eng
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Zusammenfassung:Abstract α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1707238