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Exploitation of differential electronic densities for the stereoselective reduction of ketones bearing a masked amino surrogate
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Chew, Renta Jonathan and Wills, Martin (2018) Exploitation of differential electronic densities for the stereoselective reduction of ketones bearing a masked amino surrogate. Journal of Catalysis, 361 . pp. 40-44. doi:10.1016/j.jcat.2018.02.014
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Official URL: http://dx.doi.org/10.1016/j.jcat.2018.02.014
Abstract
A tethered ruthenium-TsDPEN catalyst is employed for the facile catalytic asymmetric reduction of α-phthalimyl-α′-ketoethers under mild conditions. Leveraging exclusively on the contrasting electronic densities on the heteroatoms, a series of enantioenriched phthalimyl ether alcohols can be obtained in generally good stereoselectivities from this challenging class of substrate. Subsequent transformation into highly valuable chiral β-amino alcohols is demonstrated to take place without significant losses in yield and optical purity.
| Item Type: | Journal Article | ||||||||
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| Subjects: | Q Science > QD Chemistry | ||||||||
| Divisions: | Faculty of Science > Chemistry | ||||||||
| Library of Congress Subject Headings (LCSH): | Enantioselective catalysis, Ruthenium catalysts, Ketones, Reduction (Chemistry), Amino alcohols | ||||||||
| Journal or Publication Title: | Journal of Catalysis | ||||||||
| Publisher: | Academic Press | ||||||||
| ISSN: | 0021-9517 | ||||||||
| Official Date: | May 2018 | ||||||||
| Dates: |
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| Date of first compliant deposit: | 28 March 2018 | ||||||||
| Volume: | 361 | ||||||||
| Page Range: | pp. 40-44 | ||||||||
| DOI: | 10.1016/j.jcat.2018.02.014 | ||||||||
| Status: | Peer Reviewed | ||||||||
| Publication Status: | Published | ||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||
| RIOXX Funder/Project Grant: |
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