期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 52, 页码 23516-23520出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202009892
关键词
amino acids; ketenes; N; O-acetals; organocatalysis; phosphoric acid
资金
- NSFC [21971026]
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
The asymmetric synthesis of beta(2,2)-amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing beta(2,2)-amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter-anion-directed catalysis. As a result, a concise, practical, and atom-economic protocol toward rapidly access to beta(2,2)-amino acids has been developed.
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