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Full Paper
Organocatalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aldehydes: Development, Mechanism and DFT Calculations
Article first published online: 24 JUL 2008
DOI: 10.1002/adsc.200800277
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Ibrahem, I., Hammar, P., Vesely, J., Rios, R., Eriksson, L. and Córdova, A. (2008), Organocatalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aldehydes: Development, Mechanism and DFT Calculations. Adv. Synth. Catal., 350: 1875–1884. doi: 10.1002/adsc.200800277
Publication History
- Issue published online: 31 JUL 2008
- Article first published online: 24 JUL 2008
- Manuscript Received: 6 MAY 2008
Funded by
- Swedish National Research Council
- Wenner-Gren Foundation
- Magn Bergvall Foundation
- Carl Trygger Foundation
Keywords:
- asymmetric catalysis;
- chiral phosphines;
- DFT calcuations;
- hydrophoshination;
- organocatalysis;
- α,β-unsaturated aldehydes
Abstract
The development and mechanism of the highly chemo- and enantioselective organocatalytic hydrophosphination reaction of α,β-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.