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Synfacts 2010(3): 0321-0321  
DOI: 10.1055/s-0029-1219323
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Magnesium Schiff Base Catalyzed Direct Asymmetric Aldol Reaction

Contributor(s): Hisashi Yamamoto, Zhi Li
T. Yoshino, H. Morimoto, G. Lu, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

Direct aldol reaction of ketones is a challenging problem because of their steric hindrance. This research described a highly efficient catalytic transformation to solve this problem. In order to overcome the steric effect of ketones, the authors used α-isothiocyanato esters as nucleophiles, which could react with the hydroxyl group after the first nucleophilic addition step to generate stable oxazolidinone products.