Synfacts 2009(1): 0066-0066  
DOI: 10.1055/s-0028-1087443
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

New Chiral Diene Ligands for Rhodium-Catalyzed Conjugate Additions

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
K. Okamoto, T. Hayashi*, V. H. Rawal*
Kyoto University, Japan and The University of Chicago, USA
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Publikationsverlauf

Publikationsdatum:
18. Dezember 2008 (online)

Significance

Recently, Hayashi and others have introduced a new class of chiral bicyclic dienes which have been shown to be superior to bisphosphines as ligands in various transition-metal- ­catalyzed reactions. Unfortunately, the synthesis of many of these ligands is not trivial, limiting their broad applicability. In the present report, ­Okamoto, Hayashi and Rawal disclose a direct, two-step route to chiral diene L1 from commercially available (R)-(-)-α-phellandrene. Remarkably, in rhodium-catalyzed conjugate addition reactions L1 displayed higher levels of selectivity than several other well-known chiral dienes.