A Single-Step Synthesis of 4-Oxazolin-2-ones and Their Use in the Construction of Polycyclic Structures Bearing Quaternary Stereocenters

作者:Santoyo Blanca M; Gonzalez Romero Carlos; Merino Omar; Martinez Palou Rafael; Fuentes Benites Aydee; Jimenez Vazquez Hugo A; Delgado Francisco; Tamariz Joaquin*
来源:European Journal of Organic Chemistry, 2009, 2009(15): 2505-2518.
DOI:10.1002/ejoc.200900114

摘要

A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of alpha-ketols and isocyanates is reported. An alternative thermal approach using, the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used.

  • 出版日期2009-5