1211540-40-7Relevant academic research and scientific papers
Enantioselective synthesis of α-methylene γ-butyrolactams using N-tert-butanesulfinamides
Dema, Haythem K.,Foubelo, Francisco,Yus, Miguel
experimental part, p. 1411 - 1421 (2011/05/14)
Indium-mediated coupling of ethyl 2-(bromomethyl)acrylate (1) and chiral N-tert-butanelsulfinylimines 2 ina saturated sodium bromide aqueous solution leads to N-tert-butanesulfinyl aminoesters 3 in high yields and diastereoselectivities. After column chro
One-pot synthesis of chiral α-methylene-γ-lactams with excellent diastereoselectivities and enantioselectivities
Shen, An,Liu, Min,Jia, Zhen-Shan,Xu, Ming-Hua,Lin, Guo-Qiang
supporting information; experimental part, p. 5154 - 5157 (2011/02/23)
An efficient one-pot asymmetric synthesis of highly substituted γ-lactams containing α-methylene groups has been successfully developed. A wide range of γ-lactams could be obtained in high yields with excellent diastereomeric ratios of up to 99:1 in favor
Stereoselective synthesis of α-methylene-γ-butyrolactams from ethyl 2-(bromomethyl)acrylate and chiral sulfinyl aldimines mediated by indium
Dema, Haythem K.,Foubelo, Francisco,Yus, Miguel
experimental part, p. 125 - 131 (2010/04/25)
The reaction of ethyl 2-(bromomethyl)acrylate (1) with chiral N-tert-butylsulfinyl aldimines 2 and indium powder in THF at 100°C for 48 h affords, after hydrolysis, a mixture of N-tert-butylsulfinyl aminoesters 3 and α-methylene-γ-butyrolactams 4. From the reaction mixture, compounds 3 were quantitatively converted to the expected butyrolactams 4 after removal of the tert-butylsulfinyl group under acidic conditions and final basic workup. The whole process takes place in high overall yields and with fairly good stereoselectivities.
