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

0348884 - ÚOCHB 2011 RIV DE eng J - Journal Article
Puget, Bertrand - Jahn, Ullrich
Beta,beta-Disilylated Sulfones as Versatile Building Blocks in Organic Chemistry – A New Sulfonyl Carbanion Transmetalation.
Synlett. -, č. 17 (2010), s. 2579-2582. ISSN 0936-5214. E-ISSN 1437-2096
Institutional research plan: CEZ:AV0Z40550506
Keywords : carbanions * transmetalation * silanes * sulfones * Julia olefination
Subject RIV: CC - Organic Chemistry
Impact factor: 2.447, year: 2010

1,3-Bis(trimethylsilyl)propyl phenyl sulfone undergoes, in contrast to all reported sulfones bearing a-hydrogen atoms, an initial ortho metalation to an aryllithium at low temperature, which transmetalates quantitatively to the corresponding a-sulfonyl organolithium intermediate. Both organolithiums react selectively with aldehydes to give the corresponding products in good to excellent yields with high selectivity.
Permanent Link: http://hdl.handle.net/11104/0189286