Ruthenium-Catalyzed Alkene–Alkyne Coupling of Disubstituted Olefins: Application to the Stereoselective Synthesis of Trisubstituted Enecarbamates

2015-01-21T00:00:00Z (GMT) by Barry M. Trost James J. Cregg
The Ru-catalyzed alkene–alkyne coupling reaction has been demonstrated to be an enabling methodology for the synthesis of complex molecules. However, to date, it has been limited to monosubstituted olefins. Herein we report the first general utilization of disubstituted olefins in the Ru-catalyzed alkene–alkyne coupling reaction by employing carbamate directing groups. The products are stereodefined trisusbstituted enecarbamates. The elaboration of these structures toward the asymmetric synthesis of complex aminocyclopentitols and 1,2-amino alcohols is discussed.