Ammonium chloride promoted Ugi four-component, five-center reaction of α-substituted α-isocyano acetic acid:: A strong solvent effect

被引:48
作者
Bonne, D [1 ]
Dekhane, M
Zhu, JP
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England
关键词
D O I
10.1021/ol0479388
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Conditions have been developed for the multicomponent synthesis of di- and tetrapeptide (7) based on the unique reactivity of a-isocyano acetic acid (4 and its alpha-substituted derivatives) by an Ugi four-component, five-center reaction. Simply mixing 4, a carbonyl compound (aldehyde or ketone, 8), and a secondary amine (9) (ratio: 1:1:2) in toluene in the presence of 1.5 equiv of ammonium chloride afforded the desired product in good to excellent yield as a mixture of two diastereomers.
引用
收藏
页码:4771 / 4774
页数:4
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