Asymmetric Mannich Reactions with in Situ Generation of Carbamate-Protected Imines by an Organic Catalyst

作者：Jun Tae Song, Hui‐Wen Shih, Li Deng · 发表于：Organic Letters · 年份：2007 · DOI：10.1021/ol062837q · 被引用次数：159 · 研究领域：Asymmetric Hydrogenation and Catalysis、Asymmetric Synthesis and Catalysis、Synthesis and Catalytic Reactions

The instability of carbamate-protected alkyl imines has greatly hampered the development of catalytic asymmetric Mannich reactions suitable for the synthesis of optically active carbamate-protected chiral alkyl amines. A highly enantioselective Mannich reaction with in situ generation of carbamate-protected imines from stable alpha-amido sulfones catalyzed by an organic catalyst was developed. This reaction provides a concise and highly enantioselective route converting aromatic and aliphatic aldehydes into optically active aryl and alkyl beta-amino acids. [reaction: see text].