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1 article(s) from Bentz, Christoph

Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups

Jakub Saadi,
Christoph Bentz,
Kai Redies,
Dieter Lentz,
Reinhold Zimmer and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1236–1242, doi:10.3762/bjoc.12.118

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Scheme 1: Planned Heck reaction of A to compound B and serendipitous discovery of the palladium-catalyzed cyc...

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Scheme 2: Synthesis of compounds A (1–6) via methyl 2-siloxycyclopropanecarboxylates D, their alkylation to E...

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Scheme 3: Palladium-catalyzed reactions of methyl ketone 1 to tetralin derivative 7 and of isopropyl-substitu...

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Scheme 4: Palladium-catalyzed cyclization of diastereomeric cyclopentanone derivatives 3a/3b to products 11a ...

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Figure 1: Molecular structure (ORTEP, [14]) of compound 12a (thermal ellipsoids at 50% probability).

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Scheme 5: Palladium-catalyzed cyclizations of diastereomeric cyclohexanone derivatives 4a and 4b leading ster...

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Figure 2: Molecular structure (ORTEP, [14]) of compound 14a (thermal ellipsoids at 50% probability).

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Scheme 6: Palladium-catalyzed cyclizations of cycloheptanone derivatives 5a and 5b leading to products 15a an...

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Figure 3: Molecular structure (ORTEP, [14]) of compound 15a (thermal ellipsoids at 50% probability).

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Figure 4: Molecular structure (ORTEP [14]) of compound 15b (thermal ellipsoids at 50% probability).

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Scheme 7: Palladium-catalyzed cyclization of p-methoxy-substituted aryl iodide 6a/6b to compound 16.

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Scheme 8: Typical palladium-catalyzed cyclization of an o-iodoaniline derivative to a tricyclic tertiary alco...

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Scheme 9: Proposed transition state (TS) explaining the stereoselective formation of cyclization products.

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Scheme 10: Possible mechanism of the reduction of palladium(II) to palladium(0) by triethylamine (additional l...

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Published 16 Jun 2016

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