The University of Southampton
University of Southampton Institutional Repository

Organocatalytic asymmetric hydrophosphination of ?,?-unsaturated aldehydes: development, mechanism and DFT calculations

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
1615-4150
1875-1884
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
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), 1875-1884. (doi:10.1002/adsc.200800277).

Record type: Article

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.

Full text not available from this repository.

More information

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
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 30 Jan 2013 09:51
Last modified: 10 Dec 2019 01:37

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×