An Efficient Synthesis of Symmetric and Unsymmetric Bis-(beta-aminoamides) via Ugi Multicomponent Reaction

作者:La Spisa Fabio; Feo Alberto; Mossetti Riccardo; Tron Gian Cesare*
来源:Organic Letters, 2012, 14(23): 6044-6047.
DOI:10.1021/ol302935y

摘要

A library of symmetrical and unsymmetrical bis-(beta-aminoamides) has been prepared starting from symmetrical secondary diamines by using a double Ugi four-component reaction. A sacrifical Mumm rearrangement, thanks to the use of 2-hydroxymethyl benzoic acid, is necessary to suppress the competing split-Ugi reaction, increasing the yield and simplifying the purification step. The scope, the reaction conditions, and the role of water in trapping the nitrilium intermediate are also discussed.

  • 出版日期2012-12-7