Show brief item record

dc.contributor.authorJoyasawal, Sipak
dc.contributor.authorMa, Donghui
dc.contributor.authorDoyle, Michael P.
dc.date.accessioned2021-06-24T14:12:14Z
dc.date.available2021-06-24T14:12:14Z
dc.date.issued6/9/2021
dc.identifierdoi: 10.3390/molecules26123520
dc.identifier.citationMolecules 26 (12): 3520 (2021)
dc.identifier.urihttps://hdl.handle.net/20.500.12588/631
dc.description.abstractA substituted donor–acceptor cyclobutenecarboxamide is synthesized with modest enantiocontrol through a chiral copper(I) complex catalyzed [3 + 1]-cycloaddition reaction of ?-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.
dc.titleChallenges in the Highly Selective [3 + 1]-Cycloaddition of an Enoldiazoacetamide to Form a Donor–Acceptor Cis-Cyclobutenecarboxamide
dc.date.updated2021-06-24T14:12:15Z
dc.description.departmentChemistry


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show brief item record