Continuous flow preparation of enantiomerically pure BINOL(s) by acylative kinetic resolution

Junshan Lai, Rifahath M. Neyyappadath, Andrew D. Smith, Miguel A. Pericàs

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

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.
Original languageEnglish
JournalAdvanced Synthesis & Catalysis
VolumeEarly View
Early online date27 Jan 2020
DOIs
Publication statusE-pub ahead of print - 27 Jan 2020

Keywords

  • Isothiourea organocatalysts
  • Kinetic resolution
  • Immobilization
  • Continuous flow
  • BINOL

Fingerprint

Dive into the research topics of 'Continuous flow preparation of enantiomerically pure BINOL(s) by acylative kinetic resolution'. Together they form a unique fingerprint.

Cite this