Issue 28, 2014
From the journal:

Organic & Biomolecular Chemistry

Organocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters†

M. Kamlar,a   S. Hybelbauerová,b   I. Císařovác  and  J. Veselý*a  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 128 43 Praha 2, Czech Republic
E-mail: jxvesely@natur.cuni.cz
Fax: +42-221951226

b Department of Teaching and Didactics of Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 128 43 Praha 2, Czech Republic

c Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 128 43 Praha 2, Czech Republic

Abstract

The highly stereoselective allylic alkylation of Morita–Baylis–Hillman carbonates with β-ketoesters catalysed by β-ICD is described. The corresponding products containing two adjacent quaternary and tertiary carbon centers were obtained in good yields with high diastereoselectivity (up to 10 : 1 dr) and enantioselectivity (up to 95% ee).

Graphical abstract: Organocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C4OB00682H
Article type
Communication
Submitted
31 Mar 2014
Accepted
22 May 2014
First published
23 May 2014

Org. Biomol. Chem., 2014,12, 5071-5076

Permissions

Request permissions

Organocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters

M. Kamlar, S. Hybelbauerová, I. Císařová and J. Veselý, Org. Biomol. Chem., 2014, 12, 5071 DOI: 10.1039/C4OB00682H

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