Show brief item record

dc.contributor.authorJoyasawal, Sipak
dc.contributor.authorDoyle, Michael
dc.contributor.authorMa, Donghui
dc.date.accessioned2021-11-15T18:44:51Z
dc.date.available2021-11-15T18:44:51Z
dc.date.issued2021-06-09
dc.identifier.citation10.3390/molecules26123520en_US
dc.identifier.issn1420-3049
dc.identifier.urihttps://hdl.handle.net/20.500.12588/720
dc.description.abstractA 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_US
dc.language.isoen_USen_US
dc.publisherMDPIen_US
dc.relation.ispartofseriesMolecules;
dc.rightsAttribution 3.0 United States*
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/us/*
dc.subjectDonor–acceptor cyclobutenecarboxamide; [3 + 1]-cycloaddition reaction; 3-siloxy-2-diazo 3-butenamides; Z-γ-substituted metallo-enolcarbene; box ligands; copper (I)en_US
dc.titleChallenges in the Highly Selective [3+1]-Cycloaddition of an Enoldiazoacetamide to Form a Donor–Acceptor cis-Cyclobutenecarboxamideen_US
dc.typeArticleen_US
dc.description.departmentChemistryen_US


Files in this item

Thumbnail
Thumbnail

This item appears in the following Collection(s)

Show brief item record

Attribution 3.0 United States
Except where otherwise noted, this item's license is described as Attribution 3.0 United States