1221972-05-9Relevant academic research and scientific papers
FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives
Guérinot, Amandine,Serra-Muns, Anna,Bensoussan, Charlélie,Reymond, Sébastien,Cossy, Janine
experimental part, p. 5024 - 5033 (2011/08/04)
A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives is described. The FeCl3·6H2O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed.
Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes
Serra-Muns, Anna,Guerinot, Amandine,Reymond, Sebastien,Cossy, Janine
supporting information; experimental part, p. 4178 - 4180 (2010/08/07)
Silica gel was found to efficiently promote the rearrangement of allylic acetates into their most stable regioisomers under microwave irradiation. The reaction is easy to perform and eco-friendly. This method was applied to the metal-free synthesis of 1,3-enynes.
FeCl3-catalyzed highly diastereoselective synthesis of substituted piperidines and tetrahydropyrans
Guerinot, Amandine,Serra-Muns, Anna,Gnamm, Christian,Bensoussan, Charlelie,Reymond, Sebastien,Cossy, Janine
supporting information; experimental part, p. 1808 - 1811 (2010/10/03)
The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.
