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2 article(s) from G. Sonsona, Isaac

Synthesis and supramolecular self-assembly of glutamic acid-based squaramides

Juan V. Alegre-Requena,
Marleen Häring,
Isaac G. Sonsona,
Alex Abramov,
Eugenia Marqués-López,
Raquel P. Herrera and
David Díaz Díaz

Beilstein J. Org. Chem. 2018, 14, 2065–2073, doi:10.3762/bjoc.14.180

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Figure 1: Chemical structures of isosteric gelators 1 and 2 previously studied [33], and squaramide-based analogu...

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Scheme 1: Synthesis of squaramide-based gelators 3 and 4.

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Figure 2: Comparison of CGC, gelation time and T_gel values corresponding to six gels made using 3 and 2 [33] as g...

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Figure 3: DFS measurements for model gels made of 3 in methanol (c = 47 g/L) and ethyl acetate (c = 36 g/L). ...

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Figure 4: Representative FESEM images of selected xerogels prepared by freeze-drying the corresponding organo...

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Full Research Paper

Published 06 Aug 2018

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The aminoindanol core as a key scaffold in bifunctional organocatalysts

Isaac G. Sonsona,
Eugenia Marqués-López and
Raquel P. Herrera

Beilstein J. Org. Chem. 2016, 12, 505–523, doi:10.3762/bjoc.12.50

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Figure 1: Different configurations of 1,2-aminoindanol 1a–d.

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Scheme 1: Asymmetric F–C alkylation catalyzed by thiourea 4.

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Figure 2: Results for the F–C reaction carried out with catalyst 4 and the structurally modified analogues, 4'...

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Figure 3: (a) Transition state TS1 originally proposed for the F–C reaction catalyzed by thiourea 4 [18]. (b) Tra...

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Scheme 2: Asymmetric F–C alkylation catalyzed by thiourea ent-4 in the presence of D-mandelic acid as a Brøns...

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Figure 4: Transition state TS2 proposed for the activation of the thiourea-based catalyst ent-4 by an externa...

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Scheme 3: Friedel–Crafts alkylation of indoles catalyzed by the chiral thioamide 6.

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Scheme 4: Scalable tandem C2/C3-annulation of indoles, catalyzed by the thioamide ent-6.

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Scheme 5: Plausible tandem process mechanism for the sequential, double Friedel–Crafts alkylation, which invo...

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Scheme 6: One-pot multisequence process that allows the synthesis of interesting compounds 14. The pharmacolo...

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Scheme 7: Reaction pathway proposed for the preparation of the compounds 14.

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Scheme 8: The enantioselective synthesis of cis-vicinal-substituted indane scaffolds 21, catalyzed by ent-6.

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Scheme 9: Asymmetric domino procedure (Michael addition/Henry cyclization), catalyzed by the thioamide ent-6 ...

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Scheme 10: The enantioselective addition of indoles 2 to α,β-unsaturated acyl phosphonates 24, a) screening of...

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Figure 5: Proposed transition state TS7 for the Friedel–Crafts reaction of indole and α,β-unsaturated acyl ph...

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Scheme 11: Study of aliphatic β,γ-unsaturated α-ketoesters 26 as substrates in the F–C alkylation of indoles c...

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Figure 6: Possible transition states TS8 and TS9 in the asymmetric addition of indoles 2 to the β,γ-unsaturat...

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Figure 7: Transition state TS10 proposed for the asymmetric addition of dialkylhydrazone 28 to the β,γ-unsatu...

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Scheme 12: Different β-hydroxylamino-based catalysts tested in a Michael addition, and the transition state TS...

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Scheme 13: Enantioselective addition of acetylacetone (36a) to nitroalkenes 3, catalyzed by 37 and the propose...

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Scheme 14: Addition of 3-oxindoles 39 to 2-amino-1-nitroethenes 40, catalyzed by 41.

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Scheme 15: Michael addition of 1,3-dicarbonyl compounds 36 to the nitroalkenes 3 catalyzed by the squaramide 43...

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Scheme 16: Asymmetric aza-Henry reaction catalyzed by the aminoindanol-derived sulfinyl urea 50.

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Figure 8: Results for the aza-Henry reaction carried out with the structurally modified catalysts 50–50''.

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Scheme 17: Diels–Alder reaction catalyzed by the aminoindanol derivative ent-41.

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Scheme 18: Asymmetric Michael addition of 3-pentanone (55a) to the nitroalkenes 3 through aminocatalysis.

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Scheme 19: Substrate scope extension for the asymmetric Michael addition between the ketones 55 and the nitroa...

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Scheme 20: A possible reaction pathway in the presence of the catalyst 56 and the plausible transition state T...

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Review

Published 14 Mar 2016

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