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Synfacts 2005(0): 0050-0050  
DOI: 10.1055/s-2005-869944
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of anti-Propionate Aldols via Radical Addition

Contributor(s): Mark Lautens, Andrew Martins
M. P. Sibi*, G. Petrovich, J. Zimmerman
North Dakota State University, Fargo, USA
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Publication History

Publication Date:
20 July 2005 (online)

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Significance

Currently, there are relatively few methods for the synthesis of anti-propionate aldols with extremely high diastereo- and enantio­selectivity. Furthermore, standard aldol reactions are performed under basic conditions; limiting the functional group compatibility of the reagents. This method employs radical addition under neutral and fairly mild reaction conditions, providing products with extremely high diastereoselectivity (generally >95:5 anti/syn) and good enantioselectivity (generally >70% ee). This high degree of selectivity was obtained with various Mg2+-based Lewis acids, alkyl halides, and vinylic substituents, presenting an interesting new route towards aldol-like products.