Abstract
N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for a-hydroxy, a-chloro, and a-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective a-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 nonoxidative 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.
Original language | English |
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Pages (from-to) | 5268-5281 |
Number of pages | 14 |
Journal | Tetrahedron |
Volume | 67 |
Issue number | 29 |
DOIs | |
Publication status | Published - 22 Jul 2011 |