Chemistry–A European Journal

Pyridine??Catalyzed Stereoselective Addition of Acyclic 1, 2??Diones to Acetylenic Esters: Synthetic and Theoretical Studies of an Unprecedented Rearrangement

AN Pillai, CH Suresh, V Nair

Index: Pillai, Abhilash N.; Suresh, Cherumuttathu H.; Nair, Vijay Chemistry - A European Journal, 2008 , vol. 14, # 19 p. 5851 - 5860

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Citation Number: 16

Abstract

Abstract A systematic study of the addition of various 1, 2-acyclic diones to activated acetylenic esters catalyzed by pyridine under mild conditions is described. This reaction provides a new protocol for the stereoselective synthesis of 1, 2-diaroyl maleates. The exclusive formation of the cis isomer is especially noteworthy. This reaction occurs through the initial generation of a pyridine–dimethyl acetylene dicarboxylate zwitterion and its ...