Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton

Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spi...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-01, Vol.10 (3), p.502-505
Main Authors: Totobenazara, Jane, Haroun, Heloua, Rémond, Julien, Adil, Karim, Dénès, Fabrice, Lebreton, Jacques, Gaulon-Nourry, Catherine, Gosselin, Pascal
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob06776a