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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Asymmetric synthesis of cyclopropanes and dihydrofurans based on phosphine oxide chemistry
David J Fox1, Sean Parris, Daniel Sejer Pedersen
1University Chemical Laboratory, Lensfield Road, Cambridge, UKCB2 1EW. djf34@cam.ac.uk
Abstract:
The asymmetric synthesis of gamma-azido trans-cyclopropyl ketones is accomplished via a short, simple and efficient sequence. The cyclopropanation step is achieved by an intramolecular nucleophilic ring closure, with a diphenylphosphinate leaving group, to give trans-cyclopropane exclusively. beta-Keto-diphenylphosphine oxides cyclise to form optically active dihydrofurans. All possible diastereoisomers of dihydrofurans can be prepared selectively starting from the same olefin.
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