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Enantioselective organocatalytic addition of azlactones to maleimides: a highly stereocontrolled entry to 2,2-disubstituted-2H-oxazol-5-ones

Enantioselective organocatalytic addition of azlactones to maleimides: a highly stereocontrolled entry to 2,2-disubstituted-2H-oxazol-5-ones
Enantioselective organocatalytic addition of azlactones to maleimides: a highly stereocontrolled entry to 2,2-disubstituted-2H-oxazol-5-ones
The first highly diastereo- and enantioselective organocatalytic synthesis of 2,2-disubstituted-2H-oxazol-5-ones is described. The addition of oxazolones to maleimides is promoted by bifunctional thiourea catalysts, which afford the corresponding 2,2-disubstituted-2H-oxazol-5-ones with total regio- and stereocontrol.
maleimides, michael addition, organocatalysis
0947-6539
9884-9889
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 (2010) Enantioselective organocatalytic addition of azlactones to maleimides: a highly stereocontrolled entry to 2,2-disubstituted-2H-oxazol-5-ones. [in special issue: in honor of Professor Jose Barluenga for his 70th birthday] Chemistry - A European Journal, 16 (32), 9884-9889. (doi:10.1002/chem.201000239). (PMID:20486106)

Record type: Article

Abstract

The first highly diastereo- and enantioselective organocatalytic synthesis of 2,2-disubstituted-2H-oxazol-5-ones is described. The addition of oxazolones to maleimides is promoted by bifunctional thiourea catalysts, which afford the corresponding 2,2-disubstituted-2H-oxazol-5-ones with total regio- and stereocontrol.

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e-pub ahead of print date: 18 May 2010
Published date: 23 August 2010
Keywords: maleimides, michael addition, organocatalysis
Organisations: Chemistry

Identifiers

Local EPrints ID: 347706
URI: http://eprints.soton.ac.uk/id/eprint/347706
ISSN: 0947-6539
PURE UUID: 455a2de1-9763-40a3-9d54-d29535a28a5d
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

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Date deposited: 29 Jan 2013 11:43
Last modified: 03 Dec 2019 01:38

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Contributors

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

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