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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

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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
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:
DateEvent
May 2018Published
9 March 2018Available
14 February 2018Accepted
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:
Project/Grant IDRIOXX Funder NameFunder ID
A*STAR International Fellowship (AIF/SE/16/001)Agency for Science, Technology and Researchhttp://dx.doi.org/10.13039/501100001348

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