Synthesis of high enantiopurity N-protected alpha-amino ketones by thiol ester-organostannane cross-coupling using pH-neutral conditions.
An efficient synthesis of high enantiopurity N-protected alpha-amino ketones is described. Complementing other studies using boronic acids and thiol esters, this Cu(I) diphenylphosphinate (CuDPP)-mediated, palladium-catalyzed coupling of alpha-amino thiol esters with aryl, heteroaryl, allyl, and alkenyl organostannanes gives N-protected alpha-amino ketones in high yields with high enantiopurity (in almost all cases) under mild and pH-neutral reaction conditions. The viability of pi-deficient heteroarylstannanes is an advantage of this reaction compared to the related boronic acid system.
Li
Hao
H
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA. chemLL1@emory.edu
Yang
Hao
H
Liebeskind
Lanny S
LS