1437657-40-3Relevant academic research and scientific papers
Synthesis of polyhydroxylated piperidine and pyrrolidine peptidomimetics via one-pot sequential lactam reduction/Joullié-Ugi reaction
Szczes?niak, Piotr,Maziarz, Elzbieta,Stecko, Sebastian,Furman, Bart?omiej
, p. 3621 - 3633 (2015/04/22)
A direct approach to the synthesis of polyhydroxylated piperidine and pyrrolidine peptidomimetics is described. The presented strategy is based on one-pot reduction of sugar-derived lactams with Schwartzs reagent followed by a multicomponent Ugi-Joullié reaction.
Chiral pyrroline-based Ugi-three-component reactions are under kinetic control
Van Rijssel, Erwin R.,Goumans, Theodorus P. M.,Lodder, Gerrit,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Codee, Jeroen D. C.
supporting information, p. 3026 - 3029 (2013/07/26)
Although it is often assumed that the stereochemistry in Ugi multicomponent reactions is determined in the final Mumm rearrangement step, experimental and computational evidence that Ugi reactions on hydroxylated pyrrolines proceed under kinetic control is reported. The stereochemistry of the reaction is established with the addition of the isocyanide to the intermediate iminium ion, whose conformation is determined by its substitution pattern.
