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Highly regio- and diastereoselective oxazol-5-one addition to nitrostyrenes

Highly regio- and diastereoselective oxazol-5-one addition to nitrostyrenes
Highly regio- and diastereoselective oxazol-5-one addition to nitrostyrenes
A convenient and novel oxazol-5-one addition to nitrostyrenes is reported. The reaction is catalyzed by tertiary amines and yields the corresponding adducts with total regio- and diastereoselectivity. The addition exclusively takes place at the C-2 position of oxazol-5-ones, furnishing diastereopure N,O-aminals.
diastereoselective catalysis, organocatalysis, heterocycles, michael addition, nitrostyrenes, n, o-aminals
1434-193X
199-203
Balaguer, Andrea-Nekane
a84552bb-50d3-48e4-8001-8ca07448868e
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Calvet, Teresa
07d81814-6e36-4aa0-9f28-db0c7e3b1849
Font-Bardía, Mercé
41a15fd1-a12e-4bfc-9d86-3e209684ed2b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Balaguer, Andrea-Nekane
a84552bb-50d3-48e4-8001-8ca07448868e
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Calvet, Teresa
07d81814-6e36-4aa0-9f28-db0c7e3b1849
Font-Bardía, Mercé
41a15fd1-a12e-4bfc-9d86-3e209684ed2b
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Balaguer, Andrea-Nekane, Companyó, Xavier, Calvet, Teresa, Font-Bardía, Mercé, Moyano, Albert and Rios, Ramon (2009) Highly regio- and diastereoselective oxazol-5-one addition to nitrostyrenes. European Journal of Organic Chemistry, 2009 (2), 199-203. (doi:10.1002/ejoc.200801005).

Record type: Article

Abstract

A convenient and novel oxazol-5-one addition to nitrostyrenes is reported. The reaction is catalyzed by tertiary amines and yields the corresponding adducts with total regio- and diastereoselectivity. The addition exclusively takes place at the C-2 position of oxazol-5-ones, furnishing diastereopure N,O-aminals.

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More information

e-pub ahead of print date: 2 December 2008
Published date: January 2009
Keywords: diastereoselective catalysis, organocatalysis, heterocycles, michael addition, nitrostyrenes, n, o-aminals
Organisations: Chemistry

Identifiers

Local EPrints ID: 347722
URI: https://eprints.soton.ac.uk/id/eprint/347722
ISSN: 1434-193X
PURE UUID: 848e7818-83ec-4647-aa47-06750f2eb988
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 12:56
Last modified: 29 Oct 2019 01:40

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