Synfacts 2011(6): 0626-0626  
DOI: 10.1055/s-0030-1260430
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Allylation of Unsaturated Methylidene Ketones

Contributor(s): Hisashi Yamamoto, Patrick Brady
L. A. Brozek, J. D. Sieber, J. P. Morken*
Boston College, Chestnut Hill, USA
Further Information

Publication History

Publication Date:
19 May 2011 (online)

Significance

Asymmetric addition of allylpinacolato borane to methylidene unsaturated ketones is accomplished in the presence of a chiral palladium catalyst. The products are obtained in good to high yield and in high enantioselectivity. Importantly, this method tolerates aryl- and alkyl-substituted substrates as well as benzyl and silyl ethers. These products should be fine to be used as chiral building blocks for complex molecule synthesis.