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Synlett 2010(17): 2579-2582  
DOI: 10.1055/s-0030-1258772
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

β,β-Disilylated Sulfones as Versatile Building Blocks in Organic Chemistry - A New Sulfonyl Carbanion Transmetalation

Bertrand Puget, Ullrich Jahn*
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo namesti 2,16610 Prague 6, Czech Republic
Fax: +420220183578; e-Mail: jahn@uochb.cas.cz;
Further Information

Publication History

Received 2 August 2010
Publication Date:
30 September 2010 (online)

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Abstract

1,3-Bis(trimethylsilyl)propyl phenyl sulfone undergoes, in contrast to all reported sulfones bearing α-hydrogen atoms, an initial ortho metalation to an aryllithium at low temperature, which transmetalates quantitatively to the corresponding α-sulfonyl organolithium intermediate. Both organolithiums react selectively with aldehydes to give the corresponding products in good to excellent yields with high selectivity.

Key words

carbanions - transmetalation - silanes - sulfones - Julia olefination

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