Synthesis of α-Trialkylsilyl Ketones

M Obayashi, K Utimoto, H Nozaki

文献索引：Obayashi,M. et al. Bulletin of the Chemical Society of Japan, 1979 , vol. 52, p. 2646 - 2652

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被引用次数: 32

摘要

The isomerization of 2-trimethylsilyl-2, 3-dialkyloxiranes occurs in the presence of MgI 2 to give α-trimethylsilyl ketones only, if one starts from (2S*, 3S*)-isomers. In contrast, however, the reaction of (2S*, 3R*)-oxiranes produces enol silyl ethers in addition to α-trimethylsilyl ketones. The reaction proceeds via the Mg salts of regioand stereoselectively produced β- iodo-β-trimethylsilyl alcohols, each diastereomer of which behaves differently. ...