An improved method for the protection of carboxylic acids as 1,1-dimethylallyl esters.
1,1-Dimethylallyl (DMA) esters of various N-protected amino acids have been synthesized using prenyldimethylsulfonium tetrafluroborate, a reagent that can be readily made and stored, in conjunction with catalytic CuBr. These reactions were complete within several hours and afforded DMA esters in high yields. As has been previously shown in our group, DMA esters represent a palladium-labile proctecting group for carboxylic acids that resists nucleophilic attack as a tert-butyl ester would.
Sedighi
Minoo
M
Department of Chemistry and Cancer Center, Purdue University, West Lafayette, Indiana 47907-2084, USA.
Calimsiz
Selçuk
S
Lipton
Mark A
MA
D002264:Carboxylic Acids / Q000737:chemistry*; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
D002264:Carboxylic Acids; D004952:Esters