A highly efficient kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation has been realized for the first time to afford chiral 3-boryl-1,2,3,4-tetrahydroquinolines and recover 2-substituted 1,2-dihydroquinolines with excellent enantioselectivities and selectivity factors of up to 569.
A Cu-catalyzed regio- and enantioselective hydroboration of 1,2-dihydroquinolines with high yields and excellent enantioselectivities (up to 98% ee) was presented. This method could be applied in the asymmetric synthesis of the important intermediates used in the enantioselective synthesis of the potential agent Sumanirole for the treatment of Parkinson's disease and of the potentially interesting positive inotropic agent (S)-903.
A Cu-catalyzed
regio- and enantioselective hydroboration of various
naphthylallylic compounds affording chiral boronates with high yields
and excellent enantioselectivities (up to 96% ee) was presented. The
utility of the boronated products is further illustrated by other
stereospecific C–B bond transformations to produce amino alcohols
and other useful compounds.
A Cu-catalyzed highly diastereo- and enantioselective methylboration of diverse heterocylic coumpounds including 1,2-dihydroquinolines, 2H-chromenes and 2H-thiochromenes has been first realized providing the corresponding organoboron compounds bearing two adjacent chiral centers...
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