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Synfacts 2009(5): 0529-0529  
DOI: 10.1055/s-0029-1216628
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Titanium-Mediated Vinylaluminum Addition to Ketones

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
D. B. Biradar, H.-M. Gau*
National Chung Hsing University, Taichung, Taiwan
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

While allyltin, -silicon, and -boron ­reagents are common for vinyl addition reactions to aldehydes, vinyl additions to less reactive ­ketones remain relatively undeveloped. Recently, the authors have shown that [AlAr3(THF)] reagents are reactive nucleophiles for the titanium-catalyzed ­addition to aldehydes and ketones. Based on Hoveyda’s work (J. Am. Chem. Soc. 2008, 130, 446), the authors report the asymmetric addition of vinylaluminum reagents to aryl methyl ketones mediated by titanium. Substrate scope is quite general, affording chiral tertiary alcohols in high yields and ee values.