Organocatalytic asymmetric hydrophosphination of ?,?-unsaturated aldehydes: development, mechanism and DFT calculations
Organocatalytic asymmetric hydrophosphination of ?,?-unsaturated aldehydes: development, mechanism and DFT calculations
The development and mechanism of the highly chemo- and enantioselective organocatalytic hydrophosphination reaction of ?,?-unsaturated aldehydes is presented. The reactions are catalyzed by protected chiral diarylprolinol derivatives and give access to optically active phosphine derivatives in high yields with up to 99% ee. The organocatalytic addition of other phosphorus nucleophiles was also investigated. The origin of the high enantioselectivity for the reaction with diphenylphosphine as the nucleophile is investigated by density functional theory calculations.
asymmetric catalysis, chiral phosphines, DFT calcuations, hydrophoshination, organocatalysis, ?, ?-unsaturated aldehydes
1875-1884
Ibrahem, Ismail
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Hammar, Peter
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Vesely, Jan
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Rios, Ramon
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Eriksson, Lars
340ffb17-9c8e-468f-acba-13219dc22c37
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
4 August 2008
Ibrahem, Ismail
3cbac9c1-431b-4a1f-8c41-92aa617254b0
Hammar, Peter
b82887fb-0424-4890-940a-2c87eefb1a0e
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Eriksson, Lars
340ffb17-9c8e-468f-acba-13219dc22c37
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
Ibrahem, Ismail, Hammar, Peter, Vesely, Jan, Rios, Ramon, Eriksson, Lars and Córdova, Armando
(2008)
Organocatalytic asymmetric hydrophosphination of ?,?-unsaturated aldehydes: development, mechanism and DFT calculations.
Advanced Synthesis & Catalysis, 350 (11-12), .
(doi:10.1002/adsc.200800277).
Abstract
The development and mechanism of the highly chemo- and enantioselective organocatalytic hydrophosphination reaction of ?,?-unsaturated aldehydes is presented. The reactions are catalyzed by protected chiral diarylprolinol derivatives and give access to optically active phosphine derivatives in high yields with up to 99% ee. The organocatalytic addition of other phosphorus nucleophiles was also investigated. The origin of the high enantioselectivity for the reaction with diphenylphosphine as the nucleophile is investigated by density functional theory calculations.
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e-pub ahead of print date: 24 July 2008
Published date: 4 August 2008
Keywords:
asymmetric catalysis, chiral phosphines, DFT calcuations, hydrophoshination, organocatalysis, ?, ?-unsaturated aldehydes
Organisations:
Chemistry
Identifiers
Local EPrints ID: 347774
URI: http://eprints.soton.ac.uk/id/eprint/347774
ISSN: 1615-4150
PURE UUID: cfd1008f-531f-4d97-9e1b-1b07075d24c7
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Date deposited: 30 Jan 2013 09:51
Last modified: 14 Mar 2024 12:51
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Contributors
Author:
Ismail Ibrahem
Author:
Peter Hammar
Author:
Jan Vesely
Author:
Lars Eriksson
Author:
Armando Córdova
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