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

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• 作者：Kenneth E. Schwieter ; Jeffrey N. Johnston
• 刊名：ACS Catalysis
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：5
• 期：11
• 页码：6559-6562
• 全文大小：371K
• ISSN：2155-5435

文摘

This report details the enantioselective synthesis of 尾-amino-伪-bromo nitroalkanes with 尾-alkyl substituents, using homogeneous catalysis to prepare either antipode. Use of a bifunctional Br酶nsted 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-伪-amino amide bearing alkyl side chains鈥攐verall, in only four steps from aldehyde. The approach also addresses an underlying incompatibility between bromonitromethane and solid hydroxide bases.