Construction of multiring frameworks by metal-free cascade reactions of stable isochromenylium tetrafluoroborate.

J Org Chem

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Published: November 2009

Efficient methodologies for constructing several multiring frameworks have been developed utilizing the cascade reactions of air-stable isochromenylium tetrafluoroborates with olefins. Successive additions of two equivalents of styrene-type olefins to isochromenylium tetrafluoroborate (ICTB) 1 have been observed and their mechanisms were proposed and discussed. Intramolecular capture of the early stage cationic intermediates by predevised heteroatoms or Friedel-Crafts donors provided two different types of bridged-ring systems.

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Source
http://dx.doi.org/10.1021/jo902051gDOI Listing

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