An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent

作者：Pinna Giovanni; Bellucci Maria Cristina; Malpezzi Luciana; Pisani Laura; Superchi Stefano; Volonterio Alessandro^*; Zanda Matteo

来源：Tetrahedron, 2011, 67(29): 5268-5281.

DOI：10.1016/j.tet.2011.05.033

• Umpolung
• Sulfoxide
• Stereoselectivity
• Pummerer reaction

N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for alpha-hydroxy, alpha-chloro, and alpha-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective alpha-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.

• 出版日期2011-7-22
• 单位河北医科大学