N-Arenesulfonyl-2-aminomethylpyrrolidines $rm{-}$ Novel Modular Ligands and Organocatalysts for Asymmetric Catalysis

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 α‐amination of propanal using diethyl azadicarboxylate (DEAD) as the amine source. The init...

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Published inAdvanced synthesis & catalysis Vol. 346; no. 9-10; pp. 1101 - 1105
Main Authors Dahlin, Nils, Bøgevig, Anders, Adolfsson, Hans
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.08.2004
WILEY‐VCH Verlag
Subjects
asymmetric catalysis
diamines
organic catalysis
pyrrolidines
sulfonamides
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Summary: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 α‐amination of propanal using diethyl azadicarboxylate (DEAD) as the amine source. The initially formed α‐aminated aldehyde was reduced in situ to the corresponding N‐aminooxazolidinone, which was obtained in moderate to high yield in up to 87% ee.
Bibliography:istex:63E2B6DDFBF2C1D1B543166B68DECF17DFA32952
ark:/67375/WNG-XKKRQH5V-X
ArticleID:ADSC200404098
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200404098