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Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation

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posted on 2008-02-15, 00:00 authored by John Limanto, C. Scott Shultz, Benjamin Dorner, Richard A. Desmond, Paul N. Devine, Shane W. Krska
Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(I)−Josiphos complex in THF under 500 psi of H2 generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio.

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