2023/11/10 by Bo-Wei Huang, Bo‐Wei Huang, Jeng-Liang Han +1 · 3 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Synthesis and Catalytic Reactions #Asymmetric Hydrogenation and Catalysis
paper · doi:10.1021/acs.joc.3c01885
A vinylogous addition reaction of allyl aryl ketones with good yields and excellent regioselectivity catalyzed by squaramide catalysts has been developed. A series of chiral tertiary alcohols and bicyclic pyrrolidones could be synthesized in good to excellent yields, enantioselectivities, and diaseteroselectivities. Both experimental results and DFT calculations indicate that 1,2-addition reaction is favorable when the reaction is employed at a lower temperature, while the 1,4-addition/cyclization pathway is favorable when the reaction is employed at a higher temperature. Furthermore, the formation of compound 4 can potentially arise from either the 1,4-addition/cyclization pathway or retro-aldol reaction of compound 3, followed by subsequent 1,4-addition/cyclization.