1316845-97-2Relevant academic research and scientific papers
Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides
Gopula, Balraj,Yang, Shu-Han,Kuo, Ting-Shen,Hsieh, Jen-Chieh,Wu, Ping-Yu,Henschke, Julian P.,Wu, Hsyueh-Liang
, p. 11050 - 11055 (2015)
Chiral rhodium catalysts comprising 2,5-diaryl- substituted bicyclo[2.2.1]diene ligands L1-L10 were utilized in the enantioselective 1,4-addition reaction of arylboronic acids to N-substituted maleimides. In the presence of 2.5mol % of RhI/L2, enantioenriched conjugate addition adducts were isolated in 72-99 % yields with 86-98 %ee. This protocol offers a convenient method to access a variety of 3-arylsuccinimides in a highly enantioselective manner. Maleimides with readily cleavable N-protecting groups were tolerated enabling the synthesis of useful synthetic intermediates. Pyrrolidine 4, a biologically active compound, and pyrrolidine 5, an ent-precursor to an HSD-1 inhibitor, were synthesized to demonstrate the utility of this method. The road to rhodium! Enantioselective conjugate addition of a range of arylboronic acids to variously N-substituted maleimides, catalyzed by RhI complexes prepared in situ using chiral bicyclo[2.2.1]diene ligands, afforded the corresponding 3-arylsuccinimides with up to 98 %ee at 50 C (see scheme).
Room-temperature Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to maleimides and enones in the presence of CF3-substituted MeOBIPHEP analogues
Le Boucher D'Herouville, Florent,Millet, Anthony,Scalone, Michelangelo,Michelet, Veronique
experimental part, p. 6925 - 6930 (2011/10/08)
A Rh-based catalytic system implying electron-poor MeOBIPHEP analogues has been developed for the 1,4-addition of boronic acids to maleimides and enones under mild conditions at room temperature and led to succinimide derivatives and arylated cyclic ketones in good to excellent yields and ee. We uncovered the crucial role of the electronic and steric properties of diphosphine ligand and observed a strong boronic acid/ligand dependency in the case of maleimide derivatives and substrate/ligand matching in the case of cyclic enones.
