Organic Letters
Organic Letters
5 years ago

Asymmetric Transfer Hydrogenation of 1,3-Alkoxy/Aryloxy Propanones Using Tethered Arene/Ru(II)/TsDPEN Complexes

Asymmetric Transfer Hydrogenation of 1,3-Alkoxy/Aryloxy Propanones Using Tethered Arene/Ru(II)/TsDPEN Complexes
Sam Forshaw, Thomas J. Brown, Martin Wills, Louis J. Diorazio, Luke Williams, Alexander J. Matthews
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00756

DOI: 10.1021/acs.orglett.7b00756

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