Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro-1H-pyrano[3,4-c]chromenes - Université de Rennes Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro-1H-pyrano[3,4-c]chromenes

Résumé

We propose the synthesis of biologically relevant hexahydro-1H-pyrano[3,4-c]chromenes, via a tandem Prins/Friedels-Crafts process, catalyzed by BF3.Et2O, starting from (E)- and (Z)-5-phenoxypent-3-en-1-ol. The diastereoselectivity of the process is controlled by the geometry of the homoallylic alcohol. We also point out that the Prins product can be obtained in high yields and good diastereoselectivity when the reaction is promoted by AlCl3 as Lewis acid in the presence of an external nucleophile.
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Dates et versions

hal-03100379 , version 1 (18-02-2021)

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Vallabhareddy Satteyyanaidu, Rapelli Chandrashekhar, B. V. Subba Reddy, Claudia Lalli. Modulating Prins Cyclization versus Tandem Prins Processes for the Synthesis of Hexahydro-1H-pyrano[3,4-c]chromenes. European Journal of Organic Chemistry, 2021, 2021 (1), pp.138-145. ⟨10.1002/ejoc.202000220⟩. ⟨hal-03100379⟩
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