Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry