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Continuous flow preparation of enantiomerically pure BINOL(s) by acylative kinetic resolution
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dc.contributor.author | Lai, Junshan | |
dc.contributor.author | Neyyappadath, Rifahath M. | |
dc.contributor.author | Smith, Andrew D. | |
dc.contributor.author | Pericàs, Miguel A. | |
dc.date.accessioned | 2021-01-27T00:37:12Z | |
dc.date.available | 2021-01-27T00:37:12Z | |
dc.date.issued | 2020-01-27 | |
dc.identifier | 265942175 | |
dc.identifier | 2d2a08ba-e442-448a-840c-1c3a16ccbca4 | |
dc.identifier | 85078733075 | |
dc.identifier | 000509518500001 | |
dc.identifier.citation | Lai , 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.201901420 | en |
dc.identifier.issn | 1615-4150 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/68280986 | |
dc.identifier.uri | https://hdl.handle.net/10023/21330 | |
dc.description | Financial 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.abstract | A 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.format.extent | 1872649 | |
dc.language.iso | eng | |
dc.relation.ispartof | Advanced Synthesis & Catalysis | en |
dc.subject | Isothiourea organocatalysts | en |
dc.subject | Kinetic resolution | en |
dc.subject | Immobilization | en |
dc.subject | Continuous flow | en |
dc.subject | BINOL | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Continuous flow preparation of enantiomerically pure BINOL(s) by acylative kinetic resolution | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1002/adsc.201901420 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2021-01-27 |
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