A facilitated cyclic ether formation and its potential application in solid-phase peptide and organic synthesis.
A "trimethyl lock" system has been known to facilitate lactonization reactions through what has been termed a stereopopulation control mechanism. We have found that a similar trimethyl lock system can also facilitate cyclic ether formation with the concomitant release of a carboxylic acid in the presence of anhydrous tetrabutylammonium fluoride. To study this base-mediated trimethyl lock-facilitated cyclic ether formation, we synthesized fifteen model compounds. All model compounds underwent base-mediated cyclic ether formation in high yields at 0 degree C to room temperature (r.t.) with the concomitant release of the attached carboxylate. Such a system potentially could be used for the development of a two-dimensional linker for solid phase peptide and organic synthesis.
Shan
D
D
Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA.
Zheng
A
A
Ballard
C E
CE
Wang
W
W
Borchardt
R T
RT
Wang
B
B
D002264:Carboxylic Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D006873:Hydroquinones / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*
D002264:Carboxylic Acids; D004988:Ethers, Cyclic; D006873:Hydroquinones; D010455:Peptides