The Pd-catalyzed regio- and enantioselective ring opening of isoprene monoxide with
primary amines as pronucleophiles is developed with good yield and enantioselectivity,
constructing a quaternary stereocenter enantioselectively. This methodology was used
as the chirality inducing key step in the asymmetric synthesis of vancosamine derivative
19. The synthesis was achieved in 9 total steps and 28.6% overall yield.
palladium catalysis - enantioselectivity - quaternary stereocenter - asymmetric synthesis
- amino sugar