N‐Arenesulfonyl‐2‐aminomethylpyrrolidines - 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 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.