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Synthesis 1991; 1991(5): 357-361
DOI: 10.1055/s-1991-26465
DOI: 10.1055/s-1991-26465
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Oxidative Rearrangement of Phosphorus Containing Tertiary Allylic Alcohols: Synthesis of (3-Oxo-1-cycloalkenyl)phosphonates, -methylphosphonates, -methyldiphenylphosphine Oxides and Their Epoxy Derivatives
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Publikationsverlauf
Publikationsdatum:
29. April 2002 (online)
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Regioselective 1,2-addition of dimethyl phosphite, diethyl (lithiomethyl)phosphonate, or (lithiomethyl)diphenylphosphine oxide to 2-cyclopenten-1-one (1a) or 2-cyclohexen-1-one (1b) affords the corresponding phosphorus containing, tertiary allylic alcohols 2-4. These, upon oxidation with chromium trioxide reagents are rearranged to the new dialkyl (3-oxo-1-cycloalkenyl)phosphonates, -methylphosphonates or [(3-oxo-1-cycloalkenyl) methyl]diphenylphosphine oxides 5-7, which are easily transformed to the corresponding epoxy derivatives 8-10.