Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.
Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.
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DOI：
10.1021/acscatal.5b01901
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发表时间：
2015
期刊：
影响因子：
12.9
通讯作者：
Johnston JN
中科院分区：
文献类型：
--
作者：
Schwieter KE;Johnston JN
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 4 steps from aldehyde. The approach also addresses an underlying incompatibility between bromonitromethane and solid hydroxide bases.
