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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A facilitated cyclic ether formation and its potential application in solid-phase peptide and organic synthesis
1Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA.
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.
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