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Asymmetric transfer hydrogenation of unsaturated ketones ; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

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Hall, Thomas Howard, Adams, Hannah, Vyas, Vijyesh K., Michael Chu, K. L. and Wills, Martin (2021) Asymmetric transfer hydrogenation of unsaturated ketones ; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects. Tetrahedron, 77 . 131771. doi:10.1016/j.tet.2020.131771

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Official URL: http://dx.doi.org/10.1016/j.tet.2020.131771

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Abstract

A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C=O group reduce the level of C=O reduction compared to C=C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Hydrogenation , Ketones -- Synthesis, Ruthenium catalysts
Journal or Publication Title: Tetrahedron
Publisher: Pergamon
ISSN: 0040-4020
Official Date: 1 January 2021
Dates:
DateEvent
1 January 2021Published
19 November 2020Available
10 November 2020Accepted
Date of first compliant deposit: 20 November 2020
Volume: 77
Article Number: 131771
DOI: 10.1016/j.tet.2020.131771
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
UNSPECIFIEDRoyal Societyhttp://dx.doi.org/10.13039/501100000288
UNSPECIFIED[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
SERB-Newton International FellowshipScience and Engineering Research Boardhttp://dx.doi.org/10.13039/501100001843

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