chaetominine and propadiene

An unprecedented asymmetric N-H functionalization of quinazolinones with allenes and allylic carbonates was successfully achieved by rhodium catalysis with the assistance of chiral bidentate diphosphine ligands. The high efficiency and practicality of this method was demonstrated by a low catalyst loading of 1 mol % as well as excellent chemo-, regio-, and enantioselectivities with broad functional group compatibility. Furthermore, this newly developed strategy was applied as key step in the first enantioselective formal total synthesis of (-)-chaetominine.

Topics: Alkadienes; Allyl Compounds; Carbonates; Catalysis; Indole Alkaloids; Molecular Structure; Quinazolinones; Rhodium; Stereoisomerism