Projects per year
Abstract
A polystyrene-supported isothiourea catalyst, based on the homogeneous catalyst HyperBTM, has been prepared and used for the acylative kinetic resolution of secondary alcohols. A wide range of alcohols, including benzylic, allylic and propargylic alcohols, cycloalkanol derivatives and a 1,2-diol, has been resolved using either propionic or isobutyric anhydride with good to excellent selectivity factors obtained (28 examples, s up to 622). The catalyst can be recovered and reused by a simple filtration and washing sequence, with no special precautions needed. The recyclability of the catalyst was demonstrated (15 cycles) with no significant loss in either activity or selectivity. The recyclable catalyst was also used for the sequential resolution of 10 different alcohols us-ing different anhydrides with no cross-contamination between cycles. Finally, successful application in a continuous flow process demonstrated the first example of an immobilized Lewis base catalyst used for the kinetic resolution of alcohols in flow.
Original language | English |
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Pages (from-to) | 1067-1075 |
Number of pages | 9 |
Journal | ACS Catalysis |
Volume | 8 |
Issue number | 2 |
Early online date | 21 Dec 2017 |
DOIs | |
Publication status | Published - 2 Feb 2018 |
Keywords
- Kinetic resolution
- Isothioureas
- Lewis base catalysis
- Polymer-supported catalysts
- Catalyst recyclability
- Acyl transfer reactions
- Enantioselective catalysis
- Continuous flow
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Dive into the research topics of 'Acylative kinetic resolution of alcohols using a recyclable polymer-supported isothiourea catalyst in batch and flow'. Together they form a unique fingerprint.Projects
- 4 Finished
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RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications
Smith, A. D. (PI)
1/01/15 → 31/12/19
Project: Fellowship
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CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
1/05/14 → 31/10/22
Project: Standard
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Modification of silicon substrates: Modification of Silicon Oxide Substrates with Functional Ultrthin Organic Films
Haehner, G. (PI) & Smith, A. D. (CoI)
31/03/13 → 30/04/16
Project: Standard
Datasets
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data underpinning "Acylative Kinetic Resolution of Alcohols Using a Recyclable Polymer-Supported Isothiourea Catalyst in Batch and Flow"
Smith, A. D. (Creator), N P, R. M. (Creator) & Greenhalgh, M. D. (Creator), University of St Andrews, 9 Jul 2017
DOI: 10.17630/5c945e1a-44ac-4c1a-8cb1-a154bcefa4c6
Dataset
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