Issue 34, 2013
From the journal:

Organic & Biomolecular Chemistry

Ligand and substrate effects during Pd-catalyzed cyclizations of alkyne-tethered cyclohexadienones†

Rodolfo Tello-Aburto,‡a   Kyle A. Kalstabakken‡a  and  Andrew M. Harned*a  

* Corresponding authors

a Department of Chemistry, University of Minnesota, 207 Pleasant St SE, Minneapolis, MN, USA
E-mail: harned@umn.edu
Fax: +1 (612) 626-7541
Tel: +1 (612) 625-1036

Abstract

The effects of ligand and substrate choice on the Pd-catalyzed cyclization of alkyne-tethered cyclohexadienones were examined. In the presence of a chiral ligand, the enantioselectivity of the desymmetrization is remarkably sensitive to structural changes in both the ligand and the substrate. Additionally, the regioselectivity of the reaction (5- vs. 6-membered ring formation) is dependent on the proximity of heteroatoms to the alkyne.

Graphical abstract: Ligand and substrate effects during Pd-catalyzed cyclizations of alkyne-tethered cyclohexadienones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3OB27491H
Article type
Paper
Submitted
22 Dec 2012
Accepted
20 May 2013
First published
22 May 2013

Org. Biomol. Chem., 2013,11, 5596-5604

Permissions

Request permissions

Ligand and substrate effects during Pd-catalyzed cyclizations of alkyne-tethered cyclohexadienones

R. Tello-Aburto, K. A. Kalstabakken and A. M. Harned, Org. Biomol. Chem., 2013, 11, 5596 DOI: 10.1039/C3OB27491H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements