Issue 60, 2013

Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction

Abstract

A palladium-catalyzed hydroamination reaction is the key step in a stereoselective synthesis of 2,5-disubstituted and 2,3,5-trisubsituted morpholines from carbamate-protected aziridines. Aziridines are selectively attacked at the more substituted position by unsaturated alcohol nucleophiles using Lewis acid catalysts. Palladium-catalyzed hydroamination of the resulting aminoalkenes gives morpholines as a single diastereomer in excellent yield.

Graphical abstract: Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction

Supplementary files

Article information

Article type
Communication
Submitted
31 May 2013
Accepted
12 Jun 2013
First published
13 Jun 2013

Chem. Commun., 2013,49, 6800-6802

Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction

A. McGhee, B. M. Cochran, T. A. Stenmark and F. E. Michael, Chem. Commun., 2013, 49, 6800 DOI: 10.1039/C3CC44117B

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