Abstract
The authors present a phase-transfer-catalyzed direct Mannich reaction of malonates with N-carbamoyl (Boc and Cbz) imines generated in situ from the corresponding α-amido sulfones (1). As imine precursors α-amido sulfones derived from variously substituted aromatic, as well as from enolizable aliphatic aldehydes can be used. Applying this strategy, a broad scope of Mannich products of the general type 2 are obtained in mostly high yields and moderate to- when Cbz groups were used - high enantioselectivities. Furthermore, these Mannich products are shown to be direct precursors of enantioenriched β-substituted N-carbamoyl-protected β-amino acids via a transesterification-decarboxylation sequence.
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