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3 article(s) from Lentz, Dieter

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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Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

Holger Erdbrink,
Elisabeth K. Nyakatura,
Susanne Huhmann,
Ulla I. M. Gerling,
Dieter Lentz,
Beate Koksch and
Constantin Czekelius

Beilstein J. Org. Chem. 2013, 9, 2009–2014, doi:10.3762/bjoc.9.236

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Scheme 1: Synthesis of optically active N-acyloxazolidinone 5 from 4,4,4-trifluorobutanoic acid. Conditions: ...

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Scheme 2: Synthesis of enantiomerically pure (2S,3S)-5-F₃Ile and (2R,3S)-5-F₃-allo-Ile. TMGA = 1,1,3,3-tetram...

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Figure 1: Retention times of Fmoc amino acids plotted against the van der Waals volume of their side chains. ...

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Figure 2: CD spectra of K-5-F₃Ile and K-Ile peptides (KX: Ac-YGGKAAAAKAXAAKAAAAK-NH₂). The K-4’-F₃Ile spectru...

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Published 02 Oct 2013

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Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

Marcin Jasiński,
Dieter Lentz and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2012, 8, 662–674, doi:10.3762/bjoc.8.74

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Scheme 1: Reactivity of N-glycosyl nitrones 1 towards dipolarophiles and nucleophiles leading to products of ...

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Scheme 2: Additions of lithiated alkoxyallenes to L-erythrose-derived nitrone 1a leading to 3,6-dihydro-2H-1,...

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Figure 1: By-products 4 and 5 isolated from the reaction of nitrone 1a with lithiated methoxyallene.

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Figure 2: Single-crystal X-ray analysis of (3R)-3a (ellipsoids are drawn at a 50% probability level).

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Figure 3: Model proposed for the addition of lithiated allenes to nitrone 1a.

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Scheme 3: Speculative mechanistic suggestion for the formation of tetrasubstituted pyrrole derivative 5.

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Scheme 4: Introduction of a 5-hydroxy group into 1,2-oxazine derivatives 3 by a hydroboration/oxidation proto...

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Scheme 5: Samarium diiodide-induced ring opening of tetrahydro-2H-1,2-oxazine derivatives 12 and 13.

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Scheme 6: Reaction of tetrahydro-2H-1,2-oxazine 18 with samarium diiodide. (a) NaH (1.4 equiv), BnBr (1.2 equ...

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Scheme 7: Attempted synthesis of pyrrolidine derivatives from precursor 13. (a) TMSCl (1.5 equiv), imidazole,...

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Scheme 8: Synthesis of TBS-protected tetrahydro-2H-1,2-oxazine 27 and its transformation into pyrrolidine der...

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Published 30 Apr 2012

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