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

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 y...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-02, Vol.73 (4), p.1639-1642
Main Authors: Limanto, John, Shultz, C. Scott, Dorner, Benjamin, Desmond, Richard A, Devine, Paul N, Krska, Shane W
Format: Article
Language:English
Subjects:
Amides - chemistry
Catalysis
Chemistry
Crystallization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogen - chemistry
Magnetic Resonance Spectroscopy
Organic chemistry
Preparations and properties
Rhenium - chemistry
Spectrophotometry, Infrared
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo702429u