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

Jane Totobenazara (1) , Heloua Haroun (1) , Julien Rémond (1) , Karim Adil (2) , Fabrice Denes (3) , Jacques Lebreton (3) , Catherine Gaulon-Nourry (1) , Pascal Gosselin (1)

1 UCO2M - Unité de chimie organique moléculaire et macromoléculaire
2 LdOF - Laboratoire des oxydes et fluorures
3 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

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.

Domaines: Chimie organique

Jane Totobenazara, Heloua Haroun, Julien Rémond, Karim Adil, Fabrice Denes, et al.. Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton. Organic & Biomolecular Chemistry, 2012, 10, pp.502-505. ⟨10.1039/c1ob06776a⟩. ⟨hal-00700155⟩