Stereoselective synthesis of spirocyclic cyclopentapyrans by the Pauson-Khand reaction on camphor tethered enynes

Sezer S., Gumrukcu Y., ŞAHİN E., TANYELİ C.

TETRAHEDRON-ASYMMETRY, vol.19, no.23, pp.2705-2710, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 19 Issue: 23
  • Publication Date: 2008
  • Doi Number: 10.1016/j.tetasy.2008.11.020
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2705-2710
  • Middle East Technical University Affiliated: Yes

Abstract

An intramolecular Pauson-Khand reaction of camphor tethered enynes derived from homoallyl, homomethallyl and homopropargyl alcohols is described. Homoallyl, homomethallyl, and homopropargyl moieties are easily constructed on the camphor carbonyl group with excellent diastereoselectivity due to endo-face selectivity, and with known stereochemistry. Each enantiomerically pure enyne affords the conformationally most stable diastereomeric spirocyclic cyclopenta[c]pyran ring system. (C) 2008 Elsevier Ltd. All rights reserved.