The University of Southampton
University of Southampton Institutional Repository

Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids

Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids
Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids
The catalytic enantioselective addition of 2-tert-butyl-4-aryl-1,3-oxazol-5-ones to maleimides is reported. The addition takes place exclusively at the C-4 position of the oxazolone ring, giving access to quaternary amino acid derivatives. The reaction is catalyzed by readily available chiral bases such as (DHQD)2PYR, rendering the final compounds in good yields and with moderate to good diastereo- and enantioselectivities. When the C-4-substituent of the 2-tert-butyl-oxazolone is an alkyl group, the regioisomeric C-2 addition product is also obtained.



1144-0546
613-618
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Calbet, Teresa
f09dc31e-22d8-4f56-9a48-6b71cdcccd27
Font-Bardía, Mercé
41a15fd1-a12e-4bfc-9d86-3e209684ed2b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Calbet, Teresa
f09dc31e-22d8-4f56-9a48-6b71cdcccd27
Font-Bardía, Mercé
41a15fd1-a12e-4bfc-9d86-3e209684ed2b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Alba, Andrea-Nekane R., Valero, Guillem, Calbet, Teresa, Font-Bardía, Mercé, Moyano, Albert and Rios, Ramon (2012) Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids. New Journal of Chemistry, 36 (3), 613-618. (doi:10.1039/c1nj20659a).

Record type: Article

Abstract

The catalytic enantioselective addition of 2-tert-butyl-4-aryl-1,3-oxazol-5-ones to maleimides is reported. The addition takes place exclusively at the C-4 position of the oxazolone ring, giving access to quaternary amino acid derivatives. The reaction is catalyzed by readily available chiral bases such as (DHQD)2PYR, rendering the final compounds in good yields and with moderate to good diastereo- and enantioselectivities. When the C-4-substituent of the 2-tert-butyl-oxazolone is an alkyl group, the regioisomeric C-2 addition product is also obtained.



Full text not available from this repository.

More information

e-pub ahead of print date: 28 November 2011
Published date: March 2012
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 344063
URI: https://eprints.soton.ac.uk/id/eprint/344063
ISSN: 1144-0546
PURE UUID: 2efcb7c8-448e-424d-b8b4-ad986587d4f0
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 15 Oct 2012 12:25
Last modified: 20 Jul 2019 00:42

Export record

Altmetrics

Contributors

Author: Andrea-Nekane R. Alba
Author: Guillem Valero
Author: Teresa Calbet
Author: Mercé Font-Bardía
Author: Albert Moyano
Author: Ramon Rios ORCID iD

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×