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By Radovan Šebesta

Content material: Ionically-tagged transition-metal catalysts; Catalysis with supported organocatalysts; Supported ionic liquid section catalysis; Metal-catalysts on soluble polymers; Catalytic dendrimers; Fluorous catalysts and chiral auxiliaries in biphasic and homogeneous structures; Aqueous-phase uneven catalysis; Non-covalent immobilization

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Enantioselective Homogeneous Supported Catalysis

Content material: Ionically-tagged transition-metal catalysts; Catalysis with supported organocatalysts; Supported ionic liquid section catalysis; Metal-catalysts on soluble polymers; Catalytic dendrimers; Fluorous catalysts and chiral auxiliaries in biphasic and homogeneous platforms; Aqueous-phase uneven catalysis; Non-covalent immobilization

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71 described TEMPO immobilized on an ionic tag 54 and used it as the catalyst for oxidations of different primary and secondary alcohols to aldehydes or ketones. 24 equiv. and 10 mol% of KBr). Reactions were performed in the mixture of [bmim]PF6 and water at 0 1C. Just 1 mol% of the catalyst was necessary to reach 90–95% yield in 5–10 min. 12 N N O 54 53 N N N Me BF4 or PF6 52 Me N N BF4 N Me BF4 COO H 55 N 56 O Catalysts with ionic tag for Morita-Baylis-Hillman reaction and alcohol oxidations. aerobic oxidation of alcohols to aldehydes or ketones.

Addition of trifluoroacetic acid as co-catalyst was necessary as just 33% of the addition product was isolated after 40 h in the experiment without TFA. Catalyst 2 was more active than analogous catalyst in which imidazole ring was not alkylated. The authors examined the possibility of using other ketones or aliphatic aldehydes as donors as well. Additions of acetone as well as 3-methylbutanal went smoothly, but the reaction with cyclopentanone was much slower and less selective. After 60 h product was isolated in 87% yield with syn/anti ratio 63:37 and 80% ee.

Over 90% yield of the product was isolated even after 6th cycle, and, what is even more interesting, diastereoselectivity as well as enantioselectivity were very high (syn/anti 95:5 and 91% ee respectively). Maltsev et al. have published49 very good organocatalyst 35 for Michael addition of dimethyl malonate to substituted cinnamic aldehyde. 10). The catalyst was easy to recover, after the reaction was over, by addition of diethyl ether to the reaction mixture. Precipitated catalyst was filtered off and reused in the next experiment.

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