40216-71-5Relevant articles and documents
Re-Engineering Organocatalysts for Asymmetric Friedel-Crafts Alkylation of Indoles through Computational Studies
Gerosa, Gabriela G.,Marcarino, Maribel O.,Spanevello, Rolando A.,Suárez, Alejandra G.,Sarotti, Ariel M.
, p. 9969 - 9978 (2020/09/03)
The discovery of efficient organocatalysts is generally carried out by thorough experimental screening of different candidates. We recently reported an efficient organocatalyst for iminium-ion-based asymmetric Diels-Alder reactions following a rational design approach. This result encouraged us to test this optimal catalyst in the mechanistically related Friedel-Crafts alkylation of indoles, but to our surprise, almost null enantioselectivity was observed. The results did not significantly improve with structurally related catalysts, and a totally unexpected facial selectivity inversion was also noticed. Using DFT calculations by modeling the competing transition structures with ONIOM, we could unravel the origins of those findings, further employed to predict the most efficient catalyst for this new transformation. The computational results were validated experimentally (up to 92:8 er), providing another successful example of a general strategy to accelerate catalyst development which still remains underexplored.
Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines
Bogdanovi?, Goran A.,Bugarinovi?, Jovana,Damljanovi?, Ivan,Mini?, Aleksandra,Pe?i?, Marko,Stevanovi?, Dragana,Todosijevi?, Anka
, (2020/03/23)
The design, synthesis, spectral and electrochemical characterization of a series of novel pyrrolidine derivatives have been described. The synthesis was achieved by 1,3-dipolar cycloaddition of azomethine ylides and ferrocene-substituted chalcones, while
Study of 1,3-dipolar cycloaddition of amino-acid azomethines and Juglone
Syngaevsky, Vadym,Karkhut, Andrew,Polovkovych, Sviatoslav,Gzella, Andrzej,Lesyk, Roman,Novikov, Volodymyr
, p. 3165 - 3173 (2020/07/27)
Novel 2,3,4,9-tetrahydro- and 4,9-dihydro-1H-benzo[f]isoindole derivatives were synthesized from Juglone and amino-acid azomethines in 74–85% yields via 1,3-dipolar cycloaddition. The stereo- and regioselectivity of cycloaddition was confirmed by NMR spec