反应机理
另一种类似的缩合剂IIDQ,可以减少此副反应。
反应实例
【Org.Process Res. Dev. 2005, 9, 499】
【The Journal of Organic Chemistry 2002, 67, 8962-8969】
【J. Am. Chem. Soc. 2005, 127, 12508–12509】
【The Journal of Organic Chemistry 2016, 81, 681-688】
另外EEDQ还可以用于酯化反应,各种氨基酸及复杂羧酸都可以进行反应。常见的醇的酯化都取得了很好的效果,也可以用于制备叔丁酯。
General Procedure for the Preparation of Ester:
EEDQ (1.2 mmol) was added to a solution of the acid (1 mmol) dissolved in alcohol (20 mL) or in chloroform (20 mL) containing excess alcohol (6 mmol). The reaction was stirred for 12 h at room
temperature or at reflux for 5 h, and the solvent was evaporated
under reduced pressure. The residue was dissolved in ethyl
acetate (20 mL), washed with 5% hydrochloric acid, and dried
with anhydrous sodium sulfate. Ethyl acetate was evaporated
under reduced pressure to afford the crude product which was
purified by short column flash silica gel chromatography. In
the case of acid-labile compounds, the acid wash was omitted
and the crude product chromatographed directly after removal
of the reaction solvent.
【J. Org. Chem. 1995, 60, 7072–7074】
编译自:Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals,Org. Process Res. Dev. 2016, 20, 140−177