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Synlett 1994; 1994(12): 985-992
DOI: 10.1055/s-1994-23070
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Tandem Transformations Initiated by the Migration of a Silyl Group. Some New Synthetic Applications of Silyloxiranes

P. Jankowski* , P. Raubo, J. Wicha
  • *Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland
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Publication Date:
22 March 2002 (online)

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The trimethylsilyl group and other silicon-containing groups are able to migrate to anionic centers within the molecule. This phenomenon is used to generate tandem processes involving a silyl group migration - a leaving group elimination in systems equipped with a silyl-, oxido-, and leaving group. Applications of silyloxiranes to synthesis involving tandem processes are described. Other synthetic applications of silyloxiranes based upon the cooperative reactions of silyl-, oxido (hydroxy) and leaving group are discussed. 1. Introduction 2. Reaction of (trimethylsilyl)oxiranes with α-sulfonyl- and related anions 3. Synthesis of polyols, involving tandem silyl group migration - elimination reactions 4. Oxidation of (trimethylsilyl)oxiranes into α-hydroxyaldehyde or acylsilane derivatives 5. Reaction of (triphenylsilyl)oxirane with α-sulfonyl anions and synthetic applications of the adducts 6. Conclusions

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