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Combining electronic and steric effects to generate hindered propargylic alcohols in high enantiomeric excess
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Vyas, Vijyesh K., Knighton, Richard C., Bhanage, Bhalchandra M. and Wills, Martin (2018) Combining electronic and steric effects to generate hindered propargylic alcohols in high enantiomeric excess. Organic Letters, 20 (4). pp. 975-978. doi:10.1021/acs.orglett.7b03884 ISSN 1523-7052.
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Official URL: http://doi.org/10.1021/acs.orglett.7b03884
Abstract
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.
Item Type: | Journal Article | |||||||||||||||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||||||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||||||||||||||
SWORD Depositor: | Library Publications Router | |||||||||||||||||||||
Library of Congress Subject Headings (LCSH): | Hydrogenation, Enantioselective catalysis, Ketones, Ruthenium compounds, Complex compounds | |||||||||||||||||||||
Journal or Publication Title: | Organic Letters | |||||||||||||||||||||
Publisher: | American Chemical Society (ACS) | |||||||||||||||||||||
ISSN: | 1523-7052 | |||||||||||||||||||||
Official Date: | 16 February 2018 | |||||||||||||||||||||
Dates: |
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Volume: | 20 | |||||||||||||||||||||
Number: | 4 | |||||||||||||||||||||
Page Range: | pp. 975-978 | |||||||||||||||||||||
DOI: | 10.1021/acs.orglett.7b03884 | |||||||||||||||||||||
Status: | Peer Reviewed | |||||||||||||||||||||
Publication Status: | Published | |||||||||||||||||||||
Reuse Statement (publisher, data, author rights): | 444754491 | |||||||||||||||||||||
Access rights to Published version: | Open Access (Creative Commons) | |||||||||||||||||||||
Date of first compliant deposit: | 22 February 2018 | |||||||||||||||||||||
Date of first compliant Open Access: | 22 February 2018 | |||||||||||||||||||||
RIOXX Funder/Project Grant: |
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