N-arenesulfonyl-2-aminomethylpyrrolidines -: Novel modular ligands and organocatalysts for asymmetric catalysis

被引：106
|
作者：
Dahlin, N [1 ]
Bogevig, A [1 ]
Adolfsson, H [1 ]
机构：
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 9-10期
关键词：
asymmetric catalysis; diamines; organic catalysis; pyrrolidines; sulfonamides;
D O I：
10.1002/adsc.200404098
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A novel series of (S)-N-arenesulfonyl-2-aminomethylpyrrolidines were prepared in high overall yield starting from N-Boc-L-proline. The mono-sulfonyldiamines were evaluated as organocatalysts in the asymmetric alpha-amination of propanal using diethyl azadicarboxylate (DEAD) as the amine source. The initially formed a-aminated aldehyde was reduced in situ to the corresponding N-aminooxazolidinone, which was obtained in moderate to high yield in up to 87% ee.
引用
收藏
页码：1101 / 1105
页数：5
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