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.
613-618
Alba, Andrea-Nekane R.
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Valero, Guillem
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Calbet, Teresa
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Font-Bardía, Mercé
41a15fd1-a12e-4bfc-9d86-3e209684ed2b
Moyano, Albert
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Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
March 2012
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), .
(doi:10.1039/c1nj20659a).
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.
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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: http://eprints.soton.ac.uk/id/eprint/344063
ISSN: 1144-0546
PURE UUID: 2efcb7c8-448e-424d-b8b4-ad986587d4f0
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Date deposited: 15 Oct 2012 12:25
Last modified: 14 Mar 2024 12:09
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Contributors
Author:
Andrea-Nekane R. Alba
Author:
Guillem Valero
Author:
Teresa Calbet
Author:
Mercé Font-Bardía
Author:
Albert Moyano
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