Utilization of the Stannyl Anionic Species Generated from Me3SiSnBu3 and X- in Organic Synthesis

Miwako Mori; Naohiro Isono; Hideaki Wakamatsu

doi:10.1055/s-1999-2592

Synlett 1999; 1999(3): 269-280
DOI: 10.1055/s-1999-2592

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Utilization of the Stannyl Anionic Species Generated from Me₃SiSnBu₃ and X^- in Organic Synthesis

Miwako Mori^* , Naohiro Isono, Hideaki Wakamatsu

^*Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan; Fax +81 (11) 7 06 49 82; E-mail: mori@pharm.hokudai.ac.jp

Abstract

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The stannyl anionic species, generated from Me₃SiSnBu₃ and R₄NX, CsF or TASF [(Et₂N)₃S⁺SiMe₃F₂ ^-], is an interesting and useful reagent in organic synthesis. This anionic species can be used for the halogen-metal exchange reaction, generating an aryl or vinyl anion. Thus a novel cyclization of aryl or vinyl halides bearing a carbonyl group in a tether was developed. On the other hand, reactive intermediates such as carbene, benzyne, and quinodimethane could be generated by 1,1-, 1,2-, or 1,4-eliminations from the corresponding dihalogenated compounds. The Michael addition of the stannyl anionic species to methyl propiolate gave methyl bis-stannyl propionate in high yield and this is a useful synthon in organic synthesis.

tributylstannyltrimethylsilane - silylstannane - stannyl anion - o-quinodimethane - bisstannylated compound

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