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Synfacts 2010(3): 0327-0327  
DOI: 10.1055/s-0029-1219334
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Allylation of Ketones Using a Spirocyclic Chiral Borate

Contributor(s): Mark Lautens, Chit Tsui
X.-R. Huang, C. Chen*, G.-H. Lee, S.-M. Peng
National Dong Hwa University, Hualien and National Taiwan University, Taipei, Taiwan, Republic of China
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

A chiral spirocyclic borate ligand 1 which incorporates a rigid framework in the bipyridyl moiety has been synthesized in a three-step protocol. The catalyst formed from chromium(II)-1 promotes the Nozaki-Hiyama allylation of alkyl and aryl ketones with high yields and enantio­selectivities. The method has a broad scope and provides an efficient access to synthetically useful chiral tertiary homoallylic alcohols.