ChemInform Abstract: β,β-Disilylated Sulfones as Versatile Building Blocks in Organic Chemistry — A New Sulfonyl Carbanion Transmetalation.

✍ Scribed by Bertrand Puget; Ullrich Jahn

• Publisher: John Wiley and Sons
• Year: 2011
• Weight: 40 KB
• Volume: 42
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.201109188

✦ Synopsis

β,β-Disilylated Sulfones as Versatile Building Blocks in Organic Chemistry -A New Sulfonyl Carbanion Transmetalation. -So far, unknown bissilylated sulfone (III) undergoes an unprecedented, initial ortho-metalation to an allyllithium at low temperature, which transmetalates quantitatively to corresponding α-sulfonyl organo-lithium compound. Both organo-lithium species react selectively with aldehydes. Directed o-metalation/nucleophilic addition reactions [→(V)], Julia olefinations [→(IX)] and Brook rearrangements [→(XI)] can be selectively addressed. -(PUGET, B.; JAHN*,