Joyasawal, SipakDoyle, MichaelMa, Donghui2021-11-152021-11-152021-06-0910.3390/molecules261235201420-3049https://hdl.handle.net/20.500.12588/720A substituted donor–acceptor cyclobutenecarboxamide is synthesized with modest enan tiocontrol through a chiral copper(I) complex catalyzed [3 + 1]-cycloaddition reaction of α-acyl diphenylsulfur ylides with 3-siloxy-2-diazo-3-butenamides. With a methyl substituent on the 4-position of the 3-butenamide, the cis-vicinal-3,4-disubstituted cyclobutenecarboxamide is formed with >20:1 diastereocontrol. Donor-acceptor 3-methyl-2-siloxycyclopropenecarboxamide is rapidly formed from the reactant enoldiazoamide and undergoes catalytic ring opening to give only the Z-γ-substituted metallo-enolcarbene. Elimination from 3-siloxy-2-diazo-3-pentenamide to form the conjugated 3-siloxy-2,4-pentadienamide is competitive but minimized at low temperature.en-USAttribution 3.0 United StatesAttribution 3.0 United Stateshttp://creativecommons.org/licenses/by/3.0/us/http://creativecommons.org/licenses/by/3.0/us/Donor–acceptor cyclobutenecarboxamide[3 + 1]-cycloaddition reaction3-siloxy-2-diazo 3-butenamidesZ-γ-substituted metallo-enolcarbenebox ligandscopper (I)donor–acceptor cyclobutenecarboxamide[3 + 1]-cycloaddition reaction3-siloxy-2-diazo 3-butenamidesZ-?-substituted metallo-enolcarbenebox ligandscopper(I)Article