The influence of high pressure on static combinatorial libraries of chiral BINOL-based macrocyclic amides

In this work we presented two-, three-, and four-substrate static combinatorial libraries (SCLs) obtained via macrocyclization of BINOL-based dimethyl ester and five alpha,omega-diaminoethers of varying lengths. We investigated the distribution of macrocyclic products and measured the conversion of ester, comparing the results under atmospheric pressure to those obtained under high pressure conditions. Overall, we found that pressurization had a great impact on the proportions between macrocyclic products, promoting diamides with smaller macrocyclic cavities, i.e. those formed with shorter diaminoethers. Furthermore, static combinatorial chemistry (SCC) approach allow us to receive various potential macrocyclic receptors in single experiment. (C) 2020 Elsevier Ltd. All rights reserved.