189363-81-3Relevant academic research and scientific papers
A convenient method for the synthesis of β,γ-unsaturated amines from alkenes via α,β-unsaturated diphenylsulfonium salts
Yamanaka, Hiroyuki,Matsuo, Jun-Ichi,Kawana, Asahi,Mukaiyama, Teruaki
, p. 626 - 627 (2007/10/03)
1,1-Disubstituted and trisubstituted alkenes were converted into the corresponding β,γ-unsaturated amines 4 via three steps: the initial formation of α,β-unsaturated diphenylsulfonium triflates 2 from alkenes and diphenyl(trifluoromethanesulfonyloxy)sulfo
Total syntheses of (-)-mesembrane and (-)-mesembrine via palladium-catalyzed enantioselective allylic substitution and zirconium-promoted cyclization
Mori,Kuroda,Zhang,Sato
, p. 3263 - 3270 (2007/10/03)
4-Arylhexahydroindole derivatives 5 were synthesized from 2-arylcyclohexenyl allylamine derivatives 4, which have a large protecting group on nitrogen, using zirconium-promoted cyclization. Reaction of 4e with Cp2ZrBu2, followed by treatment with MeMgBr and then O2, gave 2a in 63% yield by a one-pot reaction, since the approach of O2 to zirconium was prevented by the aryl group. The total syntheses of (+)-mesembrane and (+)-mesembrine were achieved starting from 2a. To synthesize these natural products in a chiral form, the starting allylamine derivative 24 (80% yield, 86% ee, recrystallized from MeOH, 99% ee with 79% recovery) was prepared from allyl carbonate 22a and N-tosylallylamine 23 using palladium-catalyzed asymmetric amination in the presence of (S)-BINAPO as a chiral ligand. (-)-Mesembrane and (-)-mesembrine were synthesized from this allylamine 24.
