Fig. 5: Computer-discovered substrate-reusing MCRs and an organocatalytic reaction.
From: Systematic, computational discovery of multicomponent and one-pot reactions
a Scheme of a MCR for the synthesis of arylated skipped dienes. Non-isolated intermediates are shown in brackets and the isolated products are framed in orange. The obtained dienes were separately acetylated for the purpose of purification. The bicyclic lactone 7a (upper right) was obtained from substituted cyclohexanone (R = allyl) and phenol substrates when MgBr·Et2O was used instead of the Pd-catalyst. b The Level 2 graph view of the path leading to the arylated diene from a. Reuse of iodophenol byproduct in Heck-coupling (with oxidative addition step marked orange) is marked with the blue arc. c Scheme of organocatalytic thiol-catalyzed sp2-azidation. Non-isolated intermediates are shown in brackets and the isolated product 8b is framed in orange. d The Level 3 graph view of the path from c. Reuse of thiol, acting as an organocatalyst, is marked with the blue arc. e Additional vinyl azides 8c–f prepared by the MCR from c using different α-bromoenones. Abbreviations: DMAP, 4-dimethylaminopyridine; TBACl, tetrabutylammonium chloride.
