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Organocatalytic asymmetric hydrophosphination of alpha,beta-unsaturated aldehydes: Development, mechanism and DFT calculations
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University.
KTH, School of Biotechnology (BIO), Theoretical Chemistry.
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University.
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University.
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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
Abstract [en]

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.
Keyword [en]
asymmetric catalysis, chiral phosphines, DFT calcuations, hydrophoshination, organocatalysis, alpha, beta-unsaturated aldehydes
National Category
Theoretical Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-26060DOI: 10.1002/adsc.200800277ISI: 000258503600030Scopus ID: 2-s2.0-53849093436OAI: oai:DiVA.org:kth-26060DiVA: diva2:369586
Note
QC 20101111Available from: 2010-11-11 Created: 2010-11-11 Last updated: 2017-12-12Bibliographically approved

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