ja511911b_si_002.pdf (3.98 MB)
Ruthenium-Catalyzed Alkene–Alkyne Coupling of Disubstituted Olefins: Application to the Stereoselective Synthesis of Trisubstituted Enecarbamates
journal contribution
posted on 2015-01-21, 00:00 authored by Barry M. Trost, James J. CreggThe
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.