Organocatalytic asymmetric hydrophosphination of alpha,beta-unsaturated aldehydes: Development, mechanism and DFT calculations
2008 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 350, no 11-12, 1875-1884 p.Article, review/survey (Refereed) Published
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.
Place, publisher, year, edition, pages
2008. Vol. 350, no 11-12, 1875-1884 p.
asymmetric catalysis, chiral phosphines, DFT calcuations, hydrophoshination, organocatalysis, alpha, beta-unsaturated aldehydes
IdentifiersURN: urn:nbn:se:kth:diva-26060DOI: 10.1002/adsc.200800277ISI: 000258503600030ScopusID: 2-s2.0-53849093436OAI: oai:DiVA.org:kth-26060DiVA: diva2:369586
QC 201011112010-11-112010-11-112010-11-11Bibliographically approved