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DOI: 10.1055/s-2008-1072669
Asymmetric Hydrogenation of Farnesol and O-Protected Derivatives
A. Wang, B. Wüstenberg, A. Pfaltz*
University of Basel and DSM Nutritional Products, Basel, Switzerland
Publication History
Publication Date:
23 April 2008 (online)
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Significance
The asymmetric hydrogenation of olefins is a useful reaction for the synthesis of optically active compounds. However, the utility of rhodium or ruthenium diphosphine catalysts is usually limited to substrates containing a coordinating group or an aryl substituent next to the double bond. The authors report a class of chiral iridium catalysts bearing pyridylphosphine ligands which do not require any coordinating group broadening the scope of the asymmetric hydrogenation. Internal trialkyl-substituted olefins and allylic alcohols are efficiently hydrogenated with facial selectivity. Different isomers of the substrate are efficiently converted into the corresponding stereoisomeric products in excellent enantioselectivities and yields.