Journal
ORGANIC LETTERS
Volume 20, Issue 4, Pages 975-978Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03884
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Funding
- PhD funding agency Department of Science & Technology (DST) INSPIRE (SRF)
- Newton Bhabha fund of the Royal Society
- EPSRC [EP/M006670/1]
- ERC under the European Union's Horizon research and innovation programme [637313]
- Warwick University
- Engineering and Physical Sciences Research Council [EP/M006670/1] Funding Source: researchfish
- EPSRC [EP/M006670/1] Funding Source: UKRI
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Tethered ruthenium-TsDPEN complexes have been applied to the catalysis of the asymmetric transfer hydrogenation of a range of aryl/acetylenic ketones. The introduction of an ortho- substituent to the aryl ring of the substrate results in a reversal of the enantioselectivity, while the introduction of two o-fluoro substituents results in an improvement to the reduction enantioselectivity, as does the replacement of a phenyl ring on the alkyne with a trimethylsilyl group. These effects are rationalized as resulting from a change in the steric properties of the aryl ring and the electronic properties of the alkyne which, when matched in the reduction transition state, combine within a window of substrate/catalyst matching to generate products of high ee.
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