dc.date.accessioned | 2020-02-11T20:07:30Z | |
dc.date.available | 2020-02-11T20:07:30Z | |
dc.date.created | 2018-12-04T09:41:11Z | |
dc.date.issued | 2019 | |
dc.identifier.citation | Wåhlander, Jakob Karl Kristoffer Amedjkouh, Mohamed Balcells, David . A DFT Perspective on Diels-Alder Organocatalysts Based on Substituted Phosphoramides. European Journal of Organic Chemistry. 2019, 442 | |
dc.identifier.uri | http://hdl.handle.net/10852/73007 | |
dc.description.abstract | Phosphoramides are an interesting alternative to the thiourea motif that has long been used in organocatalysis. In the R1N(H)-P(O)(R3)-N(H)R2 formulation, phosphoramides give the advantage of having a third variable substituent, R3, compared to the two available in thioureas, and the possibility of introducing chirality with an asymmetric phosphorous center. In this work, we present a systematic computational study on the catalytic properties of these underexplored compounds. These studies show the catalytic potential of a series of substituted phosphoramides in Diels-Alder reactions, including the asymmetric [4+2] cycloaddition of pro-chiral substrates. The nature of the phosphorous-bound R3 substituent has a significant impact both on catalytic activity and enantioselectivity. Remarkably, several of the phosphoramides studied are predicted to be more active than the Schreiner’s thiourea organocatalyst. | |
dc.language | EN | |
dc.publisher | Wiley - VCH Verlag GmbH | |
dc.title | A DFT Perspective on Diels-Alder Organocatalysts Based on Substituted Phosphoramides | |
dc.type | Journal article | |
dc.creator.author | Wåhlander, Jakob Karl Kristoffer | |
dc.creator.author | Amedjkouh, Mohamed | |
dc.creator.author | Balcells, David | |
cristin.unitcode | 185,15,12,0 | |
cristin.unitname | Kjemisk institutt | |
cristin.ispublished | true | |
cristin.fulltext | preprint | |
cristin.qualitycode | 1 | |
dc.identifier.cristin | 1638765 | |
dc.identifier.bibliographiccitation | info:ofi/fmt:kev:mtx:ctx&ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=European Journal of Organic Chemistry&rft.volume=&rft.spage=442&rft.date=2019 | |
dc.identifier.jtitle | European Journal of Organic Chemistry | |
dc.identifier.volume | 2019 | |
dc.identifier.issue | 2-3 | |
dc.identifier.startpage | 442 | |
dc.identifier.endpage | 450 | |
dc.identifier.doi | https://doi.org/10.1002/ejoc.201800844 | |
dc.identifier.urn | URN:NBN:no-76118 | |
dc.type.document | Tidsskriftartikkel | |
dc.source.issn | 1434-193X | |
dc.identifier.fulltext | Fulltext https://www.duo.uio.no/bitstream/handle/10852/73007/4/PhosphoMS-1.pdf | |
dc.type.version | SubmittedVersion | |
dc.relation.project | NOTUR/NORSTORE/NN4654K | |
dc.relation.project | NFR/262695 | |