Challenges in the Highly Selective [3+1]-Cycloaddition of an Enoldiazoacetamide to Form a Donor–Acceptor cis-Cyclobutenecarboxamide
| dc.contributor.author | Joyasawal, Sipak | |
| dc.contributor.author | Doyle, Michael | |
| dc.contributor.author | Ma, Donghui | |
| dc.date.accessioned | 2021-11-15T18:44:51Z | |
| dc.date.available | 2021-11-15T18:44:51Z | |
| dc.date.issued | 2021-06-09 | |
| dc.description.abstract | A 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.description.department | Chemistry | en_US |
| dc.identifier.citation | 10.3390/molecules26123520 | en_US |
| dc.identifier.issn | 1420-3049 | |
| dc.identifier.uri | https://hdl.handle.net/20.500.12588/720 | |
| dc.language.iso | en_US | en_US |
| dc.publisher | MDPI | en_US |
| dc.relation.ispartofseries | Molecules; | |
| dc.rights | Attribution 3.0 United States | * |
| dc.rights | Attribution 3.0 United States | |
| dc.rights.uri | http://creativecommons.org/licenses/by/3.0/us/ | * |
| dc.rights.uri | http://creativecommons.org/licenses/by/3.0/us/ | |
| dc.subject | Donor–acceptor cyclobutenecarboxamide | en_US |
| dc.subject | [3 + 1]-cycloaddition reaction | en_US |
| dc.subject | 3-siloxy-2-diazo 3-butenamides | en_US |
| dc.subject | Z-γ-substituted metallo-enolcarbene | en_US |
| dc.subject | box ligands | en_US |
| dc.subject | copper (I) | en_US |
| dc.subject | donor–acceptor cyclobutenecarboxamide | |
| dc.subject | [3 + 1]-cycloaddition reaction | |
| dc.subject | 3-siloxy-2-diazo 3-butenamides | |
| dc.subject | Z-?-substituted metallo-enolcarbene | |
| dc.subject | box ligands | |
| dc.subject | copper(I) | |
| dc.title | Challenges in the Highly Selective [3+1]-Cycloaddition of an Enoldiazoacetamide to Form a Donor–Acceptor cis-Cyclobutenecarboxamide | en_US |
| dc.type | Article | en_US |