Nils Dahlin, A. Bøgevig, H. Adolfsson
Aug 1, 2004
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Journal
Advanced Synthesis & Catalysis
Abstract
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.