Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols
Abstract
The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.
Citation
Harrer , S , Greenhalgh , M D , Neyyappadath , R M & Smith , A D 2019 , ' Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols ' , Synlett , vol. 30 , no. 13 , pp. 1555-1560 . https://doi.org/10.1055/s-0037-1610721
Publication
Synlett
Status
Peer reviewed
ISSN
0936-5214Type
Journal article
Description
Authors thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, R.M.N.) for funding. We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (A.D.S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.Collections
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