β-Amino Ester Enolate as an Acrylate Anion Equivalent for the Synthesis of α-Methylene Esters, Acids, and Lactones
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.
Yu, Lin-Chen,Helquist, Paul
p. 4536 - 4541
(2007/10/02)
Synthesis and properties of some hypotensive N-alkylaminopropionic esters and N,N-dialkylaminopropionic esters and their hydroxamic acids.
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Coutts,Hubbard,Midha,Prasad
p. 28 - 33
(2007/10/04)
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