494802-99-2Relevant academic research and scientific papers
An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent
Pinna, Giovanni,Bellucci, Maria Cristina,Malpezzi, Luciana,Pisani, Laura,Superchi, Stefano,Volonterio, Alessandro,Zanda, Matteo
experimental part, p. 5268 - 5281 (2011/08/06)
N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.
An umpolung sulfoxide reagent as α-hydroxy and α-chloro benzyl carbanion equivalents
Volonterio, Alessandro,Bravo, Pierfrancesco,Zanda, Matteo
, p. 6537 - 6540 (2007/10/03)
ortho-[(N-Methyl)carbamoyl]phenyl benzyl sulfoxide is used as a synthetic equivalent of α-hydroxy and α-chloro benzyl carbanions by means of a two-step sequence involving (1) highly stereoselective α-C-alkylation with alkyl bromides, and (2) displacement of the sulfinyl group by an OH or a Cl under Pummerer or chloro-Pummerer conditions, respectively. The sulfinyl auxiliary can be effectively regenerated and recycled.
