Stereoselective synthesis of optically active cyclopenta[c]pyrans and cyclopenta[c]furans by the intramolecular Pauson-Khand reaction


Sezer S., ŞAHİN E., TANYELİ C.

TETRAHEDRON-ASYMMETRY, vol.21, no.4, pp.476-485, 2010 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 4
  • Publication Date: 2010
  • Doi Number: 10.1016/j.tetasy.2010.02.016
  • Title of Journal : TETRAHEDRON-ASYMMETRY
  • Page Numbers: pp.476-485

Abstract

An intramolecular Pauson-Khand reaction of enynes derived from homoallyl, homopropargyl, and allyl alcohols is described. 2-Heteroaryl-substituted homoallyl, homopropargyl, and allyl alcohols are easily and efficiently resolved through enzymatic resolution in high ee (91-99%) and with a known stereochemistry. Each enantiomerically enriched enyne derived from homoallyl and homopropargyl alcohols affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system as the sole product, whereas enantiomerically enriched enynes derived from allyl alcohols give a diastereomeric cis:trans mixture of the cyclopenta[c]furan ring system. (C) 2010 Elsevier Ltd. All rights reserved.