Bronsted Acid Catalyzed Enantioselective Three-Component Reaction Involving the α Addition of Isocyanides to Imines

被引:149
|
作者
Yue, Tao [1 ,2 ]
Wang, Mei-Xiang [1 ,2 ]
Wang, De-Xian [1 ,2 ]
Masson, Geraldine [3 ]
Zhu, Jieping [3 ]
机构
[1] Chinese Acad Sci, Inst Chem, Biol Chem Lab, Natl Nat Lab Mol Sci, Beijing 100190, Peoples R China
[2] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphrous Chem & Chem Biol, Beijing 100084, Peoples R China
[3] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
基金
美国国家科学基金会;
关键词
asymmetric synthesis; heterocycles; multicomponent reactions; organocatalysis; Ugi reaction; TERMINAL CARBOXYLIC-ACID; FRIEDEL-CRAFTS REACTION; MULTICOMPONENT REACTIONS; AMINO-ACID; ASYMMETRIC-SYNTHESIS; BIARYL ETHER; RAPID ACCESS; CONSTRUCTION; 5-AMINOOXAZOLE; MACROCYCLES;
D O I
10.1002/anie.200902385
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
All three together now: Three-component reactions of aldehydes, anilines, and α-isocyanoacetamides in the presence of a catalytic amount of chiral phosphoric acid afforded the 5-(1-aminoalkyl)-5-aminooxazole 1 in excellent yields and moderate to good enantiomeric excess (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KCaA.
引用
收藏
页码:6717 / 6721
页数:5
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