A simple primary-secondary diamine organocatalyst catalyzes the cascade Michael–aldol–dehydration of chalcones and unmodified ketones to produce substituted cyclohex-2-enones under mild conditions with good yields and high enantio- and/or diastereoselectivities. The success of the catalyst system is possibly due to simultaneous activation of the electrophilic chalcone by iminium formation and the nucleophilic ketone by enamine formation with an overall intramolecular iminium–di-enamine mechanism.
Pd 0 catalyst O O O O RO OTf O O O O RO Ar Ar-B(OH) 2 13 examples up to 84% yield anti-cancer screening O O O O MeO O selective inhibitior of HeLa (IC 50 = 6.7 μM) MCF-7 (IC 50 = 6.4 μM) HL-60 (IC 50 = 5.8 μM) cancer cells proliferation Abstract The C2-arylation of L-ascorbic acid, via the Suzuki cross-coupling reaction of 3-O-alkyl-5,6-O-isopropylidene-2-O-triflyl-L-ascorbic acid with boronic acids, was investigated. Various arylboronic acids were efficiently coupled under the present protocol. The biological screening results revealed that these compounds were selective anticancer agents. The most potent compound (R)-5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(furan-2-yl)-4-methoxyfuran-2(5H)-one exhibits IC 50 values of 6.7, 6.4, and 5.8 μM against human cervical cell line (HeLa), breast cancer cell line (MCF-7), and leukemic cell line (HL-60), respectively.
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