125216-89-9Relevant 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
Radical carbonylation of ω-alkynylamines leading to α-methylene lactams. Synthetic scope and the mechanistic insights
Ryu, Ilhyong,Fukuyama, Takahide,Tojino, Mami,Uenoyama, Yoshitaka,Yonamine, Yuka,Terasoma, Nozomi,Matsubara, Hiroshi
supporting information; experimental part, p. 3780 - 3786 (2011/06/27)
Tin hydride mediated radical carbonylation and cyclization reaction was investigated using a variety of ω-alkynyl amines as substrates. In this reaction α-methylene and α-stannylmethylene lactams having five to eight membered rings were obtained as princi
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.
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
Enantioselective addition of β-functionalized allylboronates to aldehydes and aldimines. Stereocontrolled synthesis of α-methylene-γ-lactones and lactams
Chataigner, Isabelle,Zammattio, Fran?oise,Lebreton, Jacques,Villiéras, Jean
, p. 2441 - 2455 (2008/09/18)
We report results regarding the development of condensations of chiral β-alkoxycarbonylallylboronates on aldehydes and imines. These allylboronates add in a highly enantioselective and diastereospecific manner to afford biologically and synthetically useful chiral α-methylene-γ-butyrolactones and lactams. The nature of the electrophile (aldehyde vs imine) is shown to have a dramatic influence on the mechanism of the reaction, probably directing the stereoselectivity of the process through different transition states.
Catalytic Asymmetric Carbalkoxyallylation of Imines with the Chiral Bis-π-allylpalladium Complex
Fernandes, Rodney A.,Yamamoto, Yoshinori
, p. 3562 - 3564 (2007/10/03)
Carbethoxyallylstannane was employed along with the bis-π -allylpalladium complex to achieve a useful conversion of prochiral imines to chiral 2-(2-aryl-2-amino-ethyl)acrylates which are improtant building blocks for further asymmetric synthesis of a wide range of compounds.
Sterecontrolled preparation of chiral secondary α-methylene γ-lactams by addition of organozinc reagents derived from 2-(bromomethyl)acrylates to imines using β-aminoalcohols as chiral auxiliaries.
Dembele, Yenimegue A.,Belaud, Chantal,Villieras, Jean
, p. 511 - 514 (2007/10/02)
Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. ca. 100percent using β-amino alcohols as chiral auxiliaries.High yields of pure R or S secondary α-methylene γ-lactams
