Polytopal Rearrangement Governing Stereochemistry of Bicyclic Oxime Ether Synthesis.

ABSTRACT: In the present study, four O-substituted oximes of quinuclidin-3-one were synthesized using appropriate O-substituted hydroxylamine hydrochlorides. In order to perform these reactions in a solvent, a mixture of (E) and (Z) products was yielded. Using mechanochemical and microwave synthesis, we then obtained pure (E) oximes. In almost all cases, the conversion to oxime ethers was completed. Reactions were monitored by ATR spectroscopy and the ratios of (E) and (Z) oxime ethers were deduced from ¹H NMR data. Several reactions were very rapid (1 min) with 100% conversion and stereospecificity. To investigate the reaction mechanisms, full conformational analyses of the reaction intermediates were performed and the lowest energy confor

SUBMITTER: Spahic Z 

PROVIDER: S-EPMC9604001 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature