Cycloisomerization of 1,6-enynes: asymmetric multistep preparation of a hydrindane framework in water with polymeric catalysts.

Org Lett

Institute for Molecular Science (IMS), CREST, and Graduate University for Advanced Studies, Higashiyama 5-1, Myodaiji, Okazaki 444-8787, Japan.

Published: January 2005

AI Article Synopsis

  • The cycloisomerization of 1,6-enynes in water using a palladium complex on a polymeric resin yielded cyclopentanes while being environmentally friendly.
  • The synthesis of a hydrindane framework involved multiple asymmetric reactions, including palladium-catalyzed processes, conducted in water with recyclable catalysts.
  • This approach emphasizes chemical greenness and efficiency by minimizing waste and utilizing water as a solvent.

Article Abstract

[Reaction: see text] Cycloisomerization of 1,6-enynes proceeded smoothly in water under heterogeneous conditions in the presence of a palladium complex supported on polystyrene-poly(ethylene glycol) copolymer resin to give the corresponding cyclopentanes with a high level of chemical greenness. Multistep asymmetric synthesis of a hydrindane framework was achieved via palladium-catalyzed asymmetric pi-allylic alkylation, propargylation, and cycloisomerization of 1,6-enynes, where all three steps were performed in water with recyclable polymeric catalysts.

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Source
http://dx.doi.org/10.1021/ol047700jDOI Listing

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