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Synfacts 2010(11): 1273-1273  
DOI: 10.1055/s-0030-1258791
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation

Contributor(s): Mark Lautens, Norman Nicolaus
S. B. Han, X. Gao, M. J. Krische*
The University of Texas at Austin, USA
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The authors report a highly anti-­diastereo- and enantioselective carbonyl (trimethylsilyl)allylation using the π-allyl (R)-SEGPHOS iridium complex (R)-I as a precatalyst. Remarkably, the same catalyst can be used to transform either primary alcohols or aldehydes into the same ­products with comparable selectivities. To avoid the undesired formation of the corresponding ­Peterson olefination products, it was essential to use K3PO4 as a base.