Oxidative Prins and Prins/Friedel-Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C-H activation. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2012

Oxidative Prins and Prins/Friedel-Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C-H activation.

Prashant Borkar
  • Fonction : Auteur
Purushotham P. Reddy
  • Fonction : Auteur
A. C. Kunwar
  • Fonction : Auteur
B. Sridhar
  • Fonction : Auteur
Basi V. Subba Reddy
  • Fonction : Auteur
  • PersonId : 943242
Jhillu S. Yadav
  • Fonction : Auteur

Résumé

1-Benzyl ethers of (E)- and (Z)-hex-3-en-1,6-diols and hept-3-en-1,7-diols undergo a smooth oxidative cyclization with DDQ in the presence of In(OTf)(3) through a sequential C-H bond activation and an intramolecular Prins cyclization to afford the corresponding trans- and cis-fused hexahydro-2H-furo[3,2-c]pyrans and octahydropyrano[4,3-b]pyrans respectively in good yields with an excellent stereoselectivity. Aryl tethered homoallylbenzyl ethers such as benzyl ethers of (E)- and (Z)-6-arylhex-3-enyl alcohols undergo a tandem Prins/Friedel-Crafts cyclization in the presence of stoichiometric amounts of DDQ and SnCl(4)via the benzylic C-H bond activation to furnish the corresponding trans- and cis-fused hexahydro-1H-benzo[f]isochromenes in good yields with complete stereoselectivity.
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Dates et versions

hal-00841533 , version 1 (05-07-2013)

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Citer

Prashant Borkar, Purushotham P. Reddy, A. C. Kunwar, B. Sridhar, René Grée, et al.. Oxidative Prins and Prins/Friedel-Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C-H activation.. Organic & Biomolecular Chemistry, 2012, 10 (7), pp.1349-58. ⟨10.1039/c1ob06489d⟩. ⟨hal-00841533⟩
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