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Asymmetric transfer hydrogenation of 1,3-alkoxy/aryloxy propanones using tethered Arene/Ru(II)/TsDPEN complexes
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Forshaw, Sam, Matthews, Alexander J., Brown, Thomas Joseph, Diorazio, Louis J., Williams, Luke and Wills, Martin (2017) Asymmetric transfer hydrogenation of 1,3-alkoxy/aryloxy propanones using tethered Arene/Ru(II)/TsDPEN complexes. Organic Letters, 19 (11). pp. 2789-2792. doi:10.1021/acs.orglett.7b00756 ISSN 1523-7060.
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Official URL: http://dx.doi.org/10.1021/acs.orglett.7b00756
Abstract
A series of propanones containing combinations of aryloxy and alkoxy substituents at the 1- and 3-positions were reduced to the alcohols via asymmetric transfer hydrogenation using a tethered Ru(II)/TsDPEN catalyst. The enantioselectivities of the reductions reveal a complex pattern of electronic and steric effects which, when used in a matched combination, can lead to the formation of products of up to 68% ee (84:16 er) from this highly challenging class of substrate.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
Library of Congress Subject Headings (LCSH): | Enantioselective catalysis , Acetone, Hydrogenation | ||||||||
Journal or Publication Title: | Organic Letters | ||||||||
Publisher: | American Chemical Society | ||||||||
ISSN: | 1523-7060 | ||||||||
Official Date: | 2 June 2017 | ||||||||
Dates: |
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Volume: | 19 | ||||||||
Number: | 11 | ||||||||
Page Range: | pp. 2789-2792 | ||||||||
DOI: | 10.1021/acs.orglett.7b00756 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 30 May 2017 | ||||||||
Date of first compliant Open Access: | 16 May 2018 | ||||||||
Funder: | University of Warwick Undergraduate Research Support Scheme, Engineering and Physical Sciences Research Council (EPSRC), AstraZeneca (Firm) |
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