Show simple item record

Files in this item

Thumbnail

Item metadata

dc.contributor.authorLai, Junshan
dc.contributor.authorNeyyappadath, Rifahath M.
dc.contributor.authorSmith, Andrew D.
dc.contributor.authorPericàs, Miguel A.
dc.date.accessioned2021-01-27T00:37:12Z
dc.date.available2021-01-27T00:37:12Z
dc.date.issued2020-01-27
dc.identifier.citationLai , J , Neyyappadath , R M , Smith , A D & Pericàs , M A 2020 , ' Continuous flow preparation of enantiomerically pure BINOL(s) by acylative kinetic resolution ' , Advanced Synthesis & Catalysis , vol. Early View . https://doi.org/10.1002/adsc.201901420en
dc.identifier.issn1615-4150
dc.identifier.otherPURE: 265942175
dc.identifier.otherPURE UUID: 2d2a08ba-e442-448a-840c-1c3a16ccbca4
dc.identifier.otherORCID: /0000-0002-2104-7313/work/68280986
dc.identifier.otherScopus: 85078733075
dc.identifier.otherWOS: 000509518500001
dc.identifier.urihttps://hdl.handle.net/10023/21330
dc.descriptionFinancial support from CERCA Programme/Generalitat de Catalunya, MINECO (CTQ2015-69136-R) and AGAUR/Generalitat de Catalunya (2017 SGR 1139) is gratefully acknowledged.en
dc.description.abstractA polystyrene‐immobilized isothiourea has been applied to the enantioselective acylative kinetic resolution (KR) of monoacylated BINOL(s) with inexpensive isobutyric anhydride in batch and flow. High selectivity values (s=29 at 0 °C) and a remarkable stability of the catalytic system in the operation conditions have been recorded for unsubstituted BINOL. No significant loss of activity/selectivity is recorded after 10 consecutive KR cycles in batch. A continuous flow process has been implemented and operated with a 100 mmol (32.8 g) sample of racemic monoacetylated BINOL in dichloromethane solution in an 84 hours experiment with a packed bed reactor containing 1 g (f=0.37 mmol.g−1) of the functional resin (s=17–21). Residence time can be decreased to 10 min with the same reactor to achieve a conversion of 58% with a selectivity factor s=17 when a more highly functionalized catalyst (f=0.88 mmol.g−1) is used. This translates into a remarkable combined productivity of 5.5 mmolprod ⋅ mmolcat−1 ⋅ h−1.
dc.language.isoeng
dc.relation.ispartofAdvanced Synthesis & Catalysisen
dc.rightsCopyright © 2020 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/adsc.201901420en
dc.subjectIsothiourea organocatalystsen
dc.subjectKinetic resolutionen
dc.subjectImmobilizationen
dc.subjectContinuous flowen
dc.subjectBINOLen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleContinuous flow preparation of enantiomerically pure BINOL(s) by acylative kinetic resolutionen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doihttps://doi.org/10.1002/adsc.201901420
dc.description.statusPeer revieweden
dc.date.embargoedUntil2021-01-27


This item appears in the following Collection(s)

Show simple item record