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Cyclic N‐sulfonyl ketimines constitute an accessible class of lead‐like heterocycles with a vast application in both synthetic organic and medicinal chemistry. In this context, we harness the capabilities of these heterocycles in four different isocyanide‐based multicomponent reactions. Our goal was to create libraries of compounds with functional groups and vectors that are compatible for structural elaboration and optimization of their physical properties. We synthesized 15 unprecedented compounds with high diversity and complexity, whereas we have obtained four single crystal structures of each scaffold, unraveling their geometrical features and potential employment in drug discovery. [ABSTRACT FROM AUTHOR]

Atropisomers have attracted a great deal of attention lately due to their numerous applications in organic synthesis and to their employment in drug discovery. However, the synthetic arsenal at our disposal with which to access them remains limited. The research described herein is two‐pronged; we both demonstrate the use of MCR chemistry as a synthetic strategy for the de novo synthesis of a class of atropisomers having high barriers to rotation with the simultaneous insertion of multiple chiral elements and we study these unprecedented molecular systems by employing a combination of crystallography, NMR and DFT calculations. By fully exploiting the synthetic capabilities of our chemistry, we have been able to monitor a range of different types of interaction, i. e. π‐π, CH–π, heteroatom‐π and CD–π, in order to conduct structure‐property studies. The results could be applied both to atroposelective synthesis and in drug discovery. [ABSTRACT FROM AUTHOR]