TY - JOUR A1 - Tichá, Iveta Chena A1 - Hybelbauerová, Simona A1 - Jindřich, Jindřich T1 - New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions JF - Beilstein Journal of Organic Chemistry PY - 2019/// VL - 15 SP - 830 EP - 839 SN - 1860-5397 DO - 10.3762/bjoc.15.80 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.15.80 KW - asymmetric allylic amination KW - cinchona alkaloids KW - CuAAC click reaction KW - cyclodextrin KW - organocatalysts N2 - The preparation of new organocatalysts for asymmetric syntheses has become a key stage of enantioselective catalysis. In particular, the development of new cyclodextrin (CD)-based organocatalysts allowed to perform enantioselective reactions in water and to recycle catalysts. However, only a limited number of organocatalytic moieties and functional groups have been attached to CD scaffolds so far. Cinchona alkaloids are commonly used to catalyze a wide range of enantioselective reactions. Thus, in this study, we report the preparation of new α- and β-CD derivatives monosubstituted with cinchona alkaloids (cinchonine, cinchonidine, quinine and quinidine) on the primary rim through a CuAAC click reaction. Subsequently, permethylated analogs of these cinchona alkaloid–CD derivatives also were synthesized and the catalytic activity of all derivatives was evaluated in several enantioselective reactions, specifically in the asymmetric allylic amination (AAA), which showed a promising enantiomeric excess of up to 75% ee. Furthermore, a new disubstituted α-CD catalyst was prepared as a pure AD regioisomer and also tested in the AAA. Our results indicate that (i) the cinchona alkaloid moiety can be successfully attached to CD scaffolds through a CuAAC reaction, (ii) the permethylated cinchona alkaloid–CD catalysts showed better results than the non-methylated CDs analogues in the AAA reaction, (iii) promising enantiomeric excesses are achieved, and (iv) the disubstituted CD derivatives performed similarly to monosubstituted CDs. Therefore, these new CD derivatives with cinchona alkaloids effectively catalyze asymmetric allylic aminations and have the potential to be successfully applied in other enantioselective reactions. ER - TY - JOUR AU - Crini, G. JF - Chem. Rev. PY - 2014/// VL - 114 SP - 10940 EP - 10975 DO - 10.1021/cr500081p ER - TY - JOUR AU - Szejtli, J. JF - Chem. Rev. PY - 1998/// VL - 98 SP - 1743 EP - 1754 DO - 10.1021/cr970022c ER - TY - JOUR AU - Breslow, R. AU - Dong, S. D. JF - Chem. Rev. PY - 1998/// VL - 98 SP - 1997 EP - 2012 DO - 10.1021/cr970011j ER - TY - JOUR AU - Easton, C. J. 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