Títol:
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Continuous Flow Preparation of Enantiomerically Pure BINOL(s) by Acylative Kinetic Resolution
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Autor/a:
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Lai, Junshan; Neyyappadath, Rifahath M.; Smith, Andrew D.; Pericàs, Miquel A.
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Abstract:
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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 oC) 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 1g (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. |
Data de publicació:
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16-01-2020 |
Matèries:
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54 |
Drets:
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L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/ |
Pàgines:
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1370 p. |
Tipus de document:
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Article Article - Versió acceptada |
DOI:
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https://doi.org/10.1002/adsc.201901420
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