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

页码：1101 / 1105

页数：5

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