One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams
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One Pot
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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.
2016 ◽
Vol 14
(2)
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pp. 556-563
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1996 ◽
Vol 37
(31)
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pp. 5483-5486
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