College of Sciences Faculty Research
Permanent URI for this collectionhttps://hdl.handle.net/20.500.12588/257
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Browsing College of Sciences Faculty Research by Subject "3-siloxy-2-diazo 3-butenamides"
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Item Challenges in the Highly Selective [3+1]-Cycloaddition of an Enoldiazoacetamide to Form a Donor–Acceptor cis-Cyclobutenecarboxamide(MDPI, 2021-06-09) Joyasawal, Sipak; Doyle, Michael; Ma, DonghuiA 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.