Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction

ÇAYİR M., Demirci S., Sezer S., TANYELİ C.

TETRAHEDRON-ASYMMETRY, vol.22, no.11, pp.1161-1168, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 11
  • Publication Date: 2011
  • Doi Number: 10.1016/j.tetasy.2011.07.003
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1161-1168
  • Middle East Technical University Affiliated: Yes


A ring closing metathesis reaction of dienes and a ring closing enyne metathesis reaction derived from allyl, homoallyl and homopropargyl alcohol backbones are described. 2-Heteroaryl substituted allyl, homoallyl and homopropargyl alcohols have been easily and efficiently resolved through enzymatic resolution with high ee (93-99%) and known stereochemistry. Enantiomerically enriched dienes derived from allyl and homoallyl alcohols afforded the corresponding enantiomerically enriched dihydrofuran and dihydropyran derivatives, respectively, with chemical yields which varied between 72% and 88%. On the other hand, enantiomerically enriched enynes derived from homoallyl and homopropargyl alcohols gave the corresponding optically active dihydropyrans with conjugated diene units with chemical yields between 70% and 80%. A subsequent Diels-Alder reaction of the dihydropyran derivatives with a diene unit with tetracyanoethylene resulted in the formation of a diastereomeric dihydroisochromene ring system as the sole product. (C) 2011 Elsevier Ltd. All rights reserved.