Elsevier

Tetrahedron

Volume 77, 1 January 2021, 131771
Tetrahedron

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

Dedicated to the memory of Professor Jonathan M. J. Williams, a brilliant scientist and a friend since our PhD years. Jon once said to me at a conference some time ago that he was trying to introduce the term “hydrogen borrowing” to synthetic chemistry, and hoped it would catch on. It certainly did.
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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 Cdouble bondO group reduce the level of Cdouble bondO reduction compared to Cdouble bondC. 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.

Keywords

Asymmetric
Catalysis
Ruthenium
Reduction
Enone
Alkyne
Enantioselective
Regioselective

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