18012-37-8Relevant academic research and scientific papers
One-Pot Alkynylation of Azaaryl Aldehydes and Spontaneous Base-Free Rearrangement into Enone Esters: an Autoinductive Mechanism
Sieng, Bora,Maldonado, Matias Funes,Romagnoli, Carlo,Amedjkouh, Mohamed
supporting information, p. 1491 - 1495 (2018/04/06)
A direct synthesis of γ-oxo-α,β-unsaturated esters has been developed. When heteroaromatic aldehydes are reacted with deprotonated ethyl propiolate, in the presence of Me2Zn or BuLi, the newly formed propargylic alcohol rearranged spontaneously to give the corresponding unsaturated keto ester. Isotope labeling, allenol intermediate trapping and crossover experiments provided insight into the reactive sequence and suggest an autocatalytic mechanism.
