Synfacts 2009(2): 0184-0184  
DOI: 10.1055/s-0028-1087508
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Oxazaborolidione-Catalyzed Asymmetric Mukaiyama Aldol Reaction of Ketones

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
S. Adachi, T. Harada*
Kyoto Institute of Technology, Japan
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Publication History

Publication Date:
22 January 2009 (online)


The authors have developed an oxazaborolidine (OXB)-catalyzed asymmetric aldol reaction of nonactivated aromatic ketones for the first time. The corresponding tertiary β-hydroxy carbonyl compounds were obtained in excellent enantioselectivities and moderate to good yields. Interestingly, the use of dimethylsilyl ketene S,O-acetal in place of the conventional trimethylsilyl derivative is found to be essential to achieve a catalytic reaction and high selectivity.