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

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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