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2 article(s) from Letzel, Matthias C

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

Matthias C. Letzel,
Hans J. Schäfer and
Roland Fröhlich

Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5

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Graphical Abstract

Figure 1: Menthol auxiliaries 1–4 used in the following anodic coupling reactions.

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Scheme 1: Synthesis of carboxylic acids 13a/b–18a/b.

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Scheme 2: (a) Preparation of benzyl 2-isopropylmalonate (5) and (b) preparation of benzyl 2-tert-butylmalonat...

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Scheme 3: Coelectrolysis (hetero-coupling) of carboxylic acids 13–17 with 3,3-dimethylbutyric acid (20).

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Figure 2: Crystal structure of the minor diastereomer 23b.

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Figure 3: Cyclic voltammograms of the malonic derivatives 15a/b, 16a/b and 18a/b (scan rate: 500 mA/s, solven...

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Scheme 4: Homo-coupling of carboxylic acids 13a/b–16a/b to diesters 26a/b/c–29a/b/c (n.d.: not determined).

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Figure 4: Crystal structure of major diastereomer 28a.

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Figure 5: Crystal structure of major diastereomer 29a.

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Figure 6: Discrimination of diastereomeric faces in the menthol substituted radical A and in the 8-phenylment...

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Scheme 5: Reductive cleavage of 30a–c to 8-phenylmenthol (3) and 31a–c.

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Supp Info

Full Research Paper

Published 05 Jan 2017

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Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system

Caterina Fraschetti,
Matthias C. Letzel,
Antonello Filippi,
Maurizio Speranza and
Jochen Mattay

Beilstein J. Org. Chem. 2012, 8, 539–550, doi:10.3762/bjoc.8.62

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Figure 1: Examples of monoexponential decay: The slope of the line directly provides the reaction pseudo-firs...

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Figure 2: Example of biexponential decay.

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Figure 3: Amidoresorcin[4]arene Y_S.

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Scheme 1: Studied (a) peptidoresorcin[4]arenes and (b) dipeptidic guests.

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Figure 4: Catharanthine and vindoline, monomers constituting the anticancer vinblastine and the analogous vin...

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Figure 5: Stable conformers of catharanthine.

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Figure 6: Global minima of (a) [V_S∙H∙T]⁺ and (b) [V_R∙H∙T]⁺ complexes.

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Figure 7: Guests studied in [47].

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Figure 8: Selected nucleosides.

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Figure 9: Example of molecular logic gate.

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Figure 10: Cyclochiral resorcin[4]arenes.

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Review

Published 12 Apr 2012

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