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Synfacts 2009(2): 0185-0185  
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

Contributor(s): Mark Lautens, Frédéric Ménard
E. A. Bercot*, S. Caille*, T. M. Bostick, K. Ranganathan, R. Jensen, M. M. Faul
Amgen Inc., Thousand Oaks, USA
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Publication History

Publication Date:
22 January 2009 (online)

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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.