Conformational control on remote stereochemistry in the intramolecular Pauson-Khand reactions of enynes tethered to homoallyl and homopropargyl alcohols


Sezer S., Ozdemirhan D., Sahin E., Tanyeli C.

TETRAHEDRON-ASYMMETRY, vol.17, no.21, pp.2981-2986, 2006 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 21
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tetasy.2006.11.012
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.2981-2986

Abstract

An intramolecular Pauson-Khand reaction of enynes derived from homoallyl and homopropargyl alcohols is described. 2-Furyl substituted homoallyl and homopropargyl alcohols are easily and efficiently resolved through enzymatic resolution in a high ee (93-99%) with a known stereochemistry. Each enantiomerically enriched enyne affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system. (c) 2006 Elsevier Ltd. All rights reserved.