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1 article(s) from Macheño, Olga García

Halides as versatile anions in asymmetric anion-binding organocatalysis

Lukas Schifferer,
Martin Stinglhamer,
Kirandeep Kaur and
Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

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Graphical Abstract

Figure 1: a) Binding interactions in the chloride channel of E. coli. and b) examples of chloride, cyanide, n...

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Figure 2: a) H-bond vs anion-binding catalysis and b) activation modes in anion-binding catalysis.

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Scheme 1: First proposed anion-binding mechanism in the thiourea-catalyzed acetalization of benzaldehyde.

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Scheme 2: a) Thiourea-catalyzed enantioselective acyl-Pictet–Spengler reaction of tryptamine-derived imines 4...

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Scheme 3: Proposed mechanism of the thiourea-catalyzed enantioselective Pictet–Spengler reaction of hydroxyla...

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Scheme 4: a) Thiourea-catalyzed intramolecular Pictet–Spengler-type cyclization of hydroxylactam-derived N-ac...

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Scheme 5: Enantioselective Reissert-type reactions of a) (iso)quinolines with silyl ketene acetals, and b) vi...

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Figure 3: Role of the counter-anion: a) Anion acting as a spectator and b) anion participating directly as th...

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Scheme 6: Enantioselective selenocyclization catalyzed by squaramide 28.

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Scheme 7: Desymmetrization of meso-aziridines catalyzed by bifunctional thiourea catalyst 31.

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Scheme 8: Anion-binding-catalyzed desymmetrization of a) meso-aziridines catalyzed by chiral triazolium catal...

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Scheme 9: Bis-urea-catalyzed enantioselective fluorination of a) β-bromosulfides and b) β-haloamines by Gouve...

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Scheme 10: a) Bifunctional thiourea anion-binding – basic/nucleophilic catalysts. Selected applications in b) ...

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Scheme 11: Thiourea-catalyzed enantioselective polycyclization reaction of hydroxylactams 51 through cation–π ...

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Scheme 12: Enantioselective aza-Sakurai cyclization of hydroxylactams 56 implicating additional cation–π and L...

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Scheme 13: Enantioselective tail-to-head cyclization of neryl chloride derivatives.

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Scheme 14: Cation–π interactions in anion binding-catalyzed asymmetric addition reactions: a) addition of indo...

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Scheme 15: Bisthiourea catalyzed oxa-Pictet–Spengler reaction of indole-based alcohols and aromatic aldehydes ...

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Scheme 16: Anion-binding catalyst development in the enantioselective addition of silyl ketene acetals to 1-ch...

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Scheme 17: a) Macrocyclic bis-thiourea catalyst in a diastereoselective glycosylation reaction. b) Competing S_N...

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Scheme 18: a) Folding mechanism of oligotriazoles upon anion recognition. b) Representative tetratriazole 82 c...

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Scheme 19: Switchable chiral tetratriazole catalyst 86 in the enantioselective addition of silyl ketene acetal...

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Review

Published 01 Sep 2021

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