Umpolung Amide Synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen AS a terminal oxidant
Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C-N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.
Schwieter, Kenneth E.,Shen, Bo,Shackleford, Jessica P.,Leighty, Matthew W.,Johnston, Jeffrey N.
Chemoselective debezylation of the N-1-phenylethyl group in 2-oxazolidinones by the anisole-methanesulfonic acid system
The chemoselective removal of N-1-phenylethyl group in 2-oxazolidinones by the anisole-methanesulfonic acid system was investigated. Optically active 4,5-cis- and 4,5-trans-diphenyl-2-oxazolidinones (1a-d) were easily synthesized from dl-stilbene oxides (trans- and cis-7a) using this debenzylation.