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Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: an asymmetric entry to ?-amino acids

Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: an asymmetric entry to ?-amino acids
Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: an asymmetric entry to ?-amino acids
The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and ?,?-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or ?-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding ?-amino acids is also described.
organocatalysis, amination reactions, ?-amino acid synthesis, isoxazolidines, asymmetric catalysis
0039-7881
1153-1157
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
Ibrahem, Ismail
3cbac9c1-431b-4a1f-8c41-92aa617254b0
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
Ibrahem, Ismail
3cbac9c1-431b-4a1f-8c41-92aa617254b0
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322

Córdova, Armando, Ibrahem, Ismail, Rios, Ramon, Vesely, Jan and Zhao, Gui-Ling (2008) Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: an asymmetric entry to ?-amino acids. Synthesis, 2008 (7), 1153-1157. (doi:10.1055/s-2007-990935).

Record type: Article

Abstract

The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and ?,?-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or ?-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding ?-amino acids is also described.

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More information

Published date: 2008
Keywords: organocatalysis, amination reactions, ?-amino acid synthesis, isoxazolidines, asymmetric catalysis
Organisations: Chemistry

Identifiers

Local EPrints ID: 347750
URI: http://eprints.soton.ac.uk/id/eprint/347750
ISSN: 0039-7881
PURE UUID: 20c8d109-3b5a-48f4-9b94-741c2ed8b2ab
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 14:30
Last modified: 29 Oct 2019 01:40

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