title: A facilitated cyclic ether formation and its potential application in solid-phase peptide and organic synthesis.
abstract: 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.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA.
authors.forename: D
authors.initials: D
authors.lastname: Shan
authors.forename: A
authors.initials: A
authors.lastname: Zheng
authors.forename: C E
authors.initials: CE
authors.lastname: Ballard
authors.forename: W
authors.initials: W
authors.lastname: Wang
authors.forename: R T
authors.initials: RT
authors.lastname: Borchardt
authors.forename: B
authors.initials: B
authors.lastname: Wang
mesh_terms: 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*
chemical_list: D002264:Carboxylic Acids; D004988:Ethers, Cyclic; D006873:Hydroquinones; D010455:Peptides