共 63 条
Asymmetric Copper(I)-Catalyzed Henry Reaction with an Aminoindanol-Derived Bisoxazolidine Ligand
被引:110
作者:

Spangler, Kimberly Yearick
论文数: 0 引用数: 0
h-index: 0
机构:
Georgetown Univ, Dept Chem, Washington, DC 20057 USA Georgetown Univ, Dept Chem, Washington, DC 20057 USA

Wolf, Christian
论文数: 0 引用数: 0
h-index: 0
机构:
Georgetown Univ, Dept Chem, Washington, DC 20057 USA Georgetown Univ, Dept Chem, Washington, DC 20057 USA
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.
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页码:4724 / 4727
页数:4
相关论文
共 63 条
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Fernandez, Isabel
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Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

Hernandez-Olmos, Victor
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Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

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