Enantioselective Synthesis of Bromocycloalkenes

  • Author: ChemistryViews.org
  • Published: 05 June 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of the American Chemical Society/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Enantioselective Synthesis of Bromocycloalkenes

Meso-compounds contain stereogenic centers, but are symmetrical overall and, thus, achiral. Reactions that break this symmetry are useful for the synthesis of chiral compounds because several stereocenters can be easily formed in one step.

Ben L. Feringa, University of Groningen, The Netherlands, and colleagues have developed such a desymmetrization reaction that converts meso-dibromocycloalkenes into chiral bromocycloalkenes (pictured). The team reacted meso-1,4-dibromocycloalk-2-enes with organolithium compounds (RLi) in the presence of a copper(I)-based catalyst with a chiral phosphoramidite ligand. The resulting asymmetric allylic substitution reaction converts the substrates into the corresponding enantioenriched substituted bromocycloalkenes.

The reaction proceeds in good yields and with high regio- and enantioselectivity (enantiomeric ratio up to 99:1). The approach can be used to generate five- and six-membered bromocycloalkenes. If seven-membered substrates are used, a ring contraction can occur during purification and the reaction leads to substituted cyclohexenes in a stereospecific manner. According to the researchers, the products can, e.g., be used for the synthesis of chiral cyclic amino alcohols, which occur in natural products and bioactive compounds.


Article Views: 780

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

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH