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Synfacts 2006(1): 0036-0036  
DOI: 10.1055/s-2005-921669
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ag(I)-Catalyzed Allylation of Ketones with Allyltrimethoxysilanes

Contributor(s): Mark Lautens, Andrew Martins
M. Wadamoto, H. Yamamoto*
The University of Chicago, USA
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

The allylation of ketones has been extensively explored; however, mild reaction conditions are rare and highly desired. This communication reports the catalytic enantioselective allylation and crotylation of a wide variety of ketones with high levels of enantioselectivity. Cyclic and acyclic aromatic ketones as well as cyclic aliphatic or α,β-unsaturated ketones worked well. Diaste­reoselection is quite high, and it is independent of the E/Z geometry of the crotyltrimethoxysilane. Interestingly, ()-3-(trimethoxysilyl)cyclohexenes afford enantioenriched products.