Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols
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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.
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
Copyright © Georg Thieme Verlag Stuttgart · New York 2019. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1055/s-0037-1610721
DescriptionAuthors 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.
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