Rh(II)/Brønsted Acid Catalyzed General and Highly Diastereo- and Enantioselective Propargylation of in SituGenerated Oxonium Ylides and C-Alkynyl N-Boc N,O-Acetals: Synthesis of Polyfunctional Propargylamines
- Resource Type
- Article
- Authors
- Meng, Xueling; Yang, Binmiao; Zhang, Linxing; Pan, Guangyao; Zhang, Xinhao; Shao, Zhihui
- Source
- Organic Letters; February 2019, Vol. 21 Issue: 5 p1292-1296, 5p
- Subject
- Language
- ISSN
- 15237060; 15237052
The first metal/organo cooperatively catalyzed asymmetric reaction of C-alkynyl N-Boc-protected N,O-acetals with in situgenerated oxonium ylides has been developed. This new type of propargylation allows for the efficient synthesis of structurally diverse unreported chiral propargylamines bearing oxa-quaternary stereocenters. The reaction features unprecedented substrate scope and high diastereo- and enantioselectivity. Theoretical studies suggest a novel cooperative catalysis model and the unique transfer of R2OH.