137869-70-6Relevant articles and documents
Water-based conditions for the microscale parallel synthesis of bicyclic lactams
Malaquin, Sandra,Jida, Mouhamad,Courtin, Justin,Laconde, Guillaume,Willand, Nicolas,Deprez, Benoit,Deprez-Poulain, Rebecca
supporting information, p. 562 - 567 (2013/02/23)
We report efficient miniaturized conditions to prepare arrays of bicyclic lactams for screening. The nature of the solvent is usually an important factor of reactivity. At a small synthesis scale, when automated pipetting devices are required, physical pr
Solvent-free microwave-assisted Meyers' lactamization
Jida, Mouhamad,Deprez-Poulain, Rebecca,Malaquin, Sandra,Roussel, Pascal,Agbossou-Niedercorn, Francine,Deprez, Benoit,Laconde, Guillaume
experimental part, p. 961 - 964 (2010/08/04)
Microwave solvent-free conditions developed for Meyers' lactamization, a typical bielectrophile-binucleophile reaction that produces quaternary centers in a stereoselective manner, give access to Meyers' chiral lactams in good yield and high diastereosele
Single and double diastereoselection in azomethine ylide cycloaddition reactions with unsaturated chiral bicyclic lactams
Fray,Meyers
, p. 3362 - 3374 (2007/10/03)
Double diastereoselectivity data were analyzed to provide insight into the structural features that influence π-facial selectivity in 1,3-dipolar cycloadditions of chiral and achiral azomethine ylides to chiral, unsaturated bicyclic lactams. Three major steric contributions to the differences in stability (ΔΔG(≠)) between competing cycloaddition transition states were identified. The first major set of steric interactions involve that between the dipoles and the substituents on the left hemisphere (R2) and concave faces of the bicyclic lactams. This effectively hindered both α- and β-approaches in the nonextended transition states. The second major steric interaction was provided by the nonbonded interactions (i) between the R1 angular substituent on the bicyclic lactam and the π-system of the dipole. This interaction was shown to be very significant, causing reversal in π-facial attack of chiral and achiral dipoles when the angular substituent is changed from phenyl or methyl to hydrogen. The high diastereoselectivity observed now opens a route to highly substituted chiral, nonracemic pyrrolidines.