Asymmetric 1,4-Addition of Oxazolones to Nitroalkenes by Bifunctional Cinchona Alkaloid Thiourea Organocatalysts: Synthesis of α,α-Disubstituted α-Amino Acids

被引:101
作者
Aleman, Jose [1 ]
Milelli, Andrea [1 ]
Cabrera, Silvia [1 ]
Reyes, Efraim [1 ]
Jorgensen, Karl Anker [1 ]
机构
[1] Aarhus Univ, Dept Chem, Danish Natl Res Fdn Ctr Catalysis, DK-8000 Aarhus C, Denmark
基金
新加坡国家研究基金会;
关键词
amino acids; organo-catalysis; oxazolones; thiourea;
D O I
10.1002/chem.200802030
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An easy and simple synthetic approach to optically active a,a-quaternary a-amino acids using asymmetric organocatalysis is presented. The addition of oxazolones to nitroalkenes catalyzed by thiourea cinchona derivatives provides the corresponding a,a-quaternary a-amino acid derivatives with good yields, excellent diastereoselectivities (up to 98% dr), and from moderate to good enantioselectivities (up to 92% ee). The reaction can be performed on a large scale. The optically active oxazolone-nitroalkene addition products can be opened in a one-pot reaction to the corresponding ester-amide derivatives. Additional transformations are also presented, such as the synthesis of amino esters, amino acids, and transformation into 3,4-disubstituted pyrrolidin-2-ones.
引用
收藏
页码:10958 / 10966
页数:9
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