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1 article(s) from Tichá, Iveta Chena

New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

Iveta Chena Tichá,
Simona Hybelbauerová and
Jindřich Jindřich

Beilstein J. Org. Chem. 2019, 15, 830–839, doi:10.3762/bjoc.15.80

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Graphical Abstract

Figure 1: Schematic cone-shaped (a) and structure representations (b) of α-CD (six glucopyranoside units) and...

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Figure 2: Common cinchona alkaloids (cinchonine, cinchonidine, quinine, quinidine).

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Scheme 1: CuAAC click reaction of propargylated cinchona alkaloids 3a–d with 6^I-azido-6^I-deoxy-α-CD (1) and 6^I...

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Scheme 2: CuAAC click reaction of per-Me-N₃-α-CD (6) or per-Me-N₃-β-CD (7) and propargylated cinchona alkaloi...

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Scheme 3: Synthesis of difunctionalized α-CD 11 with quinine moieties.

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Figure 3: Representative ¹H NMR spectrum of the non-methylated quinidine–α-CD derivative 4d.

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Figure 4: Representative ¹³C NMR spectrum and parts of the HMBC spectrum of the non-methylated quinidine–α-CD...

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Scheme 4: AAA reaction of MBH carbamate 12 catalyzed by the prepared CD derivatives 4a–d, 5a–d, 8a–d, 9a–d, 11...

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Published 01 Apr 2019

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