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- W2951567391 abstract "Asymmetric processes, taking place via the intermediacy of chiral oxonium ions arising from intramolecular haloetherification reactions of chiral ene- and diene-acetals of optically pure C 2-symmetric hydrobenzoine, have been developed. A novel, double intramolecular haloetherification process was observed. The asymmetric reactions developed in this effort were applied to the synthesis of several natural products, including solenopsin A, (cis-6-methyltetrahydropyran-2-yl)acetic acid, the pheromone of the wasp Paravespula vulgaris, rubrenolide, rubrynolide, scyphostatin, cryptocaryone, Sch 642305, and clavolonine. The strategies used in these syntheses involved a new concept called ‘chiral auxiliary multiple-use methodology’. In addition, intramolecular haloetherification reactions of ene-acetals, derived from chiral optically pure norbornene aldehydes and meso-diols, were applied to asymmetric desymmetrization of meso-diols. Finally, a new method for the resolution of racemic norbornene aldehydes, utilizing chiral ene-acetal oxonium ion intermediates produced from optically pure hydrobenzoin, was developed." @default.
- W2951567391 created "2019-06-27" @default.
- W2951567391 creator A5027099765 @default.
- W2951567391 date "2012-03-15" @default.
- W2951567391 modified "2023-10-16" @default.
- W2951567391 title "Intramolecular Haloetherification of Ene- and Diene-Acetals: Asymmetric Synthesis Involving Chiral Oxonium Ion Intermediates" @default.
- W2951567391 doi "https://doi.org/10.1055/s-0031-1290620" @default.
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