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Synfacts 2009(2): 0185-0185
DOI: 10.1055/s-0028-1087643
DOI: 10.1055/s-0028-1087643
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Quaternary Center Formation via Diastereoselective Arylation of Enolates
E. A. Bercot*, S. Caille*, T. M. Bostick, K. Ranganathan, R. Jensen, M. M. Faul
Amgen Inc., Thousand Oaks, USA
Further Information
Publication History
Publication Date:
22 January 2009 (online)
Significance
The construction of all-carbon quaternary centers is the challenge addressed using a commercial catalyst in a simple procedure. Impressively, the reaction allows the arylation of enolates where diastereoselectivity is controlled by a remote group. Various aryl and alkenyl bromides can be added to cyclohexyl enolates with synthetically useful stereoselectivity. Complex functionalized cyclohexyl derivatives can be prepared from simple reagents.