Highly Chemo- and Stereoselective Alkenylative Cyclization

  • Author: Claire D'Andola
  • Published Date: 05 September 2013
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Highly Chemo- and Stereoselective Alkenylative Cyclization

Related Societies

Transition-metal-catalyzed cyclization of 1,6-enynes is a powerful method for constructing carbo- and heterocyclic molecules. Cyclization of 1,6-enynes with main-group organometallics or metal hydrides is particularly attractive because these reactions offer new approaches for the highly stereoselective formation of ring systems with exocyclic tri- or tetrasubstituted C–C double bonds. Despite developments in this area, the use of inexpensive metal catalysts for these reactions remains in high demand.


Chien-Hong Cheng and co-workers, National Tsing Hua University, Taiwan, describe a low-cost, highly chemo- and stereoselective nickel-catalyzed tandem cyclization/coupling of electronically unactivated 1,6-enynes with alkenyl boronic acids to provide various substituted pyrrolidines and dihydrofurans, which are found in a variety of natural products and biologically active molecules.

A variety of alkenyl boronic acids were successfully employed and elucidation of the reaction mechanism provided evidence for chemoselective protonation of the nickelacyclopentene intermediate leading to the addition of the alkenyl group of the boronic acid at the alkene terminus of the 1,6-enyne in the final product. Further studies to expand the scope of the tandem cyclization are currently underway.


Article Views: 3145

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH