Mild Conversion of Esters Lacking Acidic alpha-Hydrogens into Amides via Samarium(III) Tris[hexamethyldisilazide] and Amines

作者：Campbell James B^*; Sparks Richard B; Dedinas Robert F

来源：Synlett, 2011, (3): 357-360.

DOI：10.1055/s-0030-1259508

• esters
• amides
• lanthanides
• HMDS
• samarium

Samarium(III) tris[ hexamethyldisilazide] (Sm[(Me(3)Si)(2)N](3) = Sm[HMDS](3)) promotes the direct conversion of an ester admixed with an amine into the corresponding carboxamide under exceptionally mild conditions (<= 0 degrees C) and in high yields. Only a slight excess of amine and the lanthanide complex are required to effect complete conversion of the ester into the amide. Esters with acidic alpha-hydrogens undergo a competing Claisen-like condensation along with the desired conversion into amides.

• 出版日期2011-2