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.

中文翻译：

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使用α，α-二氟-β-内酰胺合成一锅开环肽

摘要

α，α-二氟-β-内酰胺成功地在2,2,2-三氟乙醇中进行了各种氨基酸的开环氨解反应，得到了含氟肽。在该氨解中，发现2,2,2-三氟乙醇首先通过裂解内酰胺环攻击α，α-二氟-β-内酰胺形成相应的开链2,2,2-三氟乙基酯作为反应性中间体。与相应的甲酯相比，三氟乙基酯更具亲电性，从而加速了各种氨基酸的氨解反应，形成了具有α，α-二氟亚甲基单元的β-氨基酸肽。