α,β-Dehydroamino Acid Synthesis through Proline-Catalyzed Aldol Condensation with a Glycine Schiff Base  

作　　者：Jun Sawamura Daikan Ieiri Ryo Yazaki Takashi Ohshima 

机构地区：[1]Graduate School of Pharmaceutical Sciences,Kyushu University,Fukuoka 812-8582,Japan

出　　处：《Precision Chemistry》2024年第1期14-20,共7页精准化学（英文）

基　　金：supported by MEXT KAKENHI grant numbers JP21A204,JP21H05207,and JP21H05208 for The Grant-in-Aid for Transformative Research Areas(A)Digitalization-driven Transformative Organic Synthesis(Digi-TOS)from MEXT,a Grant-in-Aid for Scientific Research(B)(JP21H02607);the JST-FOREST program(JPMJFR2229);a Grant-in-Aid for Basis for Supporting Innovative Drug Discovery and Life Science Research(BINDS)(JP20am0101091,JP22ama121031)and AMED(JP21ak0101167,JP22ak0101167,JP23ak0101167);J.S.thanks the Japan Science and Technology Agency(JST)SPRING(JPMJSP2136).

摘　　要：A general protocol for the synthesis ofα,β-dehydroamino acids and their peptides was developed.Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes.The hydroxy group on the benzophenone imine was crucial for high Z/E selectivity and further transimination for protecting group-freeα,β-dehydroamino esters.Peptide elongation of both the C-and N-terminals highlighted the usefulness of our present protocol.

关 键 词：α β-dehydroamino acid PEPTIDE PROLINE aldol condensation glycine Schiff base transimination 

分 类 号：O62[理学—有机化学]