78804-68-9Relevant academic research and scientific papers
USE OF METHYL 3-(N,N-DIMETHYLAMINO)PROPIONATE AS A SYNTHON FOR THE CONSTRUCTION OF α-METHYLENE γ-BUTYROLACTONES
Yu, Lin-Chen,Helquist, Paul
, p. 591 - 598 (2007/10/02)
The lithium enolate of methyl 3-(N,N-dimethylamino)propionate reacts with allylic halides to give alkylation products which may be converted into α-methylene γ-butyrolactones by a reaction sequence which includes iodolactonization among other simple steps.
β-Amino Ester Enolate as an Acrylate Anion Equivalent for the Synthesis of α-Methylene Esters, Acids, and Lactones
Yu, Lin-Chen,Helquist, Paul
, p. 4536 - 4541 (2007/10/02)
The lithium enolate (18) of methyl 3-(dimethylamino)propionate (17) has been developed as a synthetic equivalent of the α-anion (15) of acrylic acid.The enolate, obtained by treatment of the free ester (17) with lithium diisopropylamide, may be alkylated with a variety of alkyl halides to give products which may be considered to be protected acrylate esters.Unmasking is accomplished by quaternization with methyl iodide followed by DBN-induced elimination to give the free acrylates.The products derived from allylic halides may conveniently be converted into α-methylene lactones.
