Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 42, Pages 11134-11138Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901262
Keywords
asymmetric catalysis; copper; enantioselectivity; silanes; reduction
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Funding
- Samsung Research Fund
- Sungkyunkwan University
- Korean Government (MOEHRD, Basic Research Promotion Fund) [KRF-2008-531-C00039]
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An efficient method for the preparation of enantiomerically enriched 1,1-diarylalkyl units has been developed. The use of copper hydride complexed by the (R)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyidicyclo- hexylphosphine (Josiphos) ligand effects a highly enantioselective conjugate reduction of beta,beta-diaryl-substituted alpha,beta-unsaturated nitriles with aryl groups of similar steric demand and no secondary coordination site. A range of substrates with meta and para substituents on the aryl group were reduced with good to excellent enantioselectivities (up to 97% enantiomeric excess (ee)) and this methodology was applied to the formal synthesis of indatraline.
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