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Enantioselective Addition of Bromonitromethane to Aliphatic N‑Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst

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journal contribution
posted on 06.11.2015, 00:00 by Kenneth E. Schwieter, Jeffrey N. Johnston
This report details the enantioselective synthesis of β-amino-α-bromo nitroalkanes with β-alkyl substituents, using homogeneous catalysis to prepare either antipode. Use of a bifunctional Brønsted base/acid catalyst allows equal access to either enantiomer of the products, enabling the use of Umpolung Amide Synthesis (UmAS) to prepare the corresponding L- or D-α-amino amide bearing alkyl side chainsoverall, in only four steps from aldehyde. The approach also addresses an underlying incompatibility between bromonitromethane and solid hydroxide bases.