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Synlett 1993; 1993(11): 841-843
DOI: 10.1055/s-1993-22627
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Formation of 1,2-Cyclopropanediols in the Reaction of Acylsilanes with Ketone Enolates

Kei Takeda* , Junko Nakatani, Hitoshi Nakamura, Koichi Sako, Eiichi Yoshii, Kentaro Yamaguchi
  • *Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-01, Japan
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Publication Date:
19 March 2002 (online)

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The reaction of benzoyl- and crotonylsilanes (5,9) with lithium enolates of methyl ketones produced 1,2-cyclopropanediols (7,10) via Brook rearrangement of the initial 1,2-adduct and subsequent internal aldol reaction. Treatment of 7 with benzaldehyde in the presence of NaN(SiMe3)2 afforded acyclic aldol adduct 12.