Projects per year
Abstract
Cyclic ketones bearing α-quaternary stereocenters undergo efficient kinetic resolution using cyclohexanone monooxygenase (CHMO) from Acinetobacter calcoaceticus. Lactones possessing tetrasubstituted stereocenters are obtained with high enantioselectivity (up to >99% ee) and complete chemoselectivity. Preparative scale biotransformations were exploited in conjunction with a SmI2-mediated cyclization process to access complex, enantiomerically enriched cycloheptan- and cycloctan-1,4-diols. In a parallel approach to structurally distinct products, enantioenriched ketones from the resolution bearing an α- all carbon quaternary stereocenter were used in a SmI2-mediated cyclization process to give cyclobutanol products (up to >99% ee).
| Original language | English |
|---|---|
| Pages (from-to) | 3692-3696 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 57 |
| Issue number | 14 |
| Early online date | 2 Feb 2018 |
| DOIs | |
| Publication status | Published - 26 Mar 2018 |
Research Beacons, Institutes and Platforms
- Manchester Institute of Biotechnology
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Dive into the research topics of 'Biocatalytic conversion of cyclic ketones bearing α-quaternary stereocenters to lactones in an enantioselective radical approach to medium-sized carbocycles'. Together they form a unique fingerprint.Projects
- 1 Finished
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Manchester Synthetic Biology Research Centre for Fine and Speciality Chemicals
Scrutton, N. (PI), Azapagic, A. (CoI), Balmer, A. (CoI), Barran, P. (CoI), Breitling, R. (CoI), Delneri, D. (CoI), Dixon, N. (CoI), Faulon, J.-L. (CoI), Flitsch, S. (CoI), Goble, C. (CoI), Goodacre, R. (CoI), Hay, S. (CoI), Kell, D. (CoI), Leys, D. (CoI), Lloyd, J. (CoI), Lockyer, N. (CoI), Martin, P. (CoI), Micklefield, J. (CoI), Munro, A. (CoI), Pedrosa Mendes, P. (CoI), Randles, S. (CoI), Salehi Yazdi, F. (CoI), Shapira, P. (CoI), Takano, E. (CoI), Turner, N. (CoI) & Winterburn, J. (CoI)
14/11/14 → 13/05/20
Project: Research