Asymmetric Copper(I)-Catalyzed Henry Reaction with an Aminoindanol-Derived Bisoxazolidine Ligand

被引:110
作者
Spangler, Kimberly Yearick [1 ]
Wolf, Christian [1 ]
机构
[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA
基金
美国国家科学基金会;
关键词
CHIRAL BUILDING-BLOCKS; ALPHA-HYDROXY ESTERS; SCHIFF-BASE LIGANDS; L-GLUTAMIC ACID; NITROALDOL REACTION; COPPER(II) COMPLEXES; CATALYST; ENANTIOSELECTIVITY; EFFICIENT; ALDEHYDES;
D O I
10.1021/ol9018612
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bisoxazolidine 1 is an effective ligand In the Me2Zn-promoted and the Cu(I)-catalyzed Henry reaction. While a wide range of nitroaldol products are obtained in high yields and ee's in both cases, the replacement of dimethylzinc with copper(l) acetate results in a complete reversal of the sense of asymmetric induction. The Cu(I)-catalyzed enantioselective addition of nitromethane to methyl 4-oxobutanoate followed by hydrogenation and spontaneous lactamization gives (S)-5-hydroxypiperidin-2-one in 72% overall yield and 98% ee which compares favorably with previously reported methods.
引用
收藏
页码:4724 / 4727
页数:4
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