Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 11-12, Pages 1875-1884Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800277
Keywords
asymmetric catalysis; chiral phosphines; DFT calcuations; hydrophoshination; organocatalysis; alpha,beta-unsaturated aldehydes
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Funding
- Swedish National Research Council
- Wenner-Gren Foundation
- Magn Bergvall Foundation
- Carl Trygger Foundation
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The development and mechanism of the highly chemo- and enantioselective organocatalytic hydrophosphination reaction of alpha,beta-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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