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3 article(s) from Pohl, Radek

Ligand-dependent stereoselective Suzuki–Miyaura cross-coupling reactions of β-enamido triflates

Tomáš Chvojka,
Athanasios Markos,
Svatava Voltrová,
Radek Pohl and
Petr Beier

Beilstein J. Org. Chem. 2021, 17, 2657–2662, doi:10.3762/bjoc.17.179

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Scheme 1: A: Synthesis of (Z)-β-enamido triflates and subsequent stereoselective cross-coupling reactions. B:...

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Scheme 2: Substrate scope of the Suzuki coupling leading to enamides 2 and 3. ^aRatio determined by ¹⁹F NMR; ^b...

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Scheme 3: Proposed mechanisms for the formed Suzuki coupling retention products 2 and inversion products 3.

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Letter

Published 29 Oct 2021

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α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

Mikhail K. Klychnikov,
Radek Pohl,
Ivana Císařová and
Ullrich Jahn

Beilstein J. Org. Chem. 2021, 17, 688–704, doi:10.3762/bjoc.17.58

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Figure 1: Selected alkaloids containing the pyrrolidone motif.

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Scheme 1: A) Classical γ-lactam synthesis by atom transfer radical cyclizations; B) previously developed tand...

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Figure 2: X-ray crystal structure of the major (2R,4S)-alkoxyamine hydrochloride derived from 9j. Displacemen...

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Scheme 2: Formation of the α-(aminoxy)amides 9o,p.

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Figure 3: X-ray crystal structure of the minor cis-diastereomers of the keto lactam 13j (left) and the hydrox...

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Scheme 3: Thermal radical cyclization reactions of amides 9l–p bearing cyclic units. Conditions: a) t-BuOH, 1...

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Scheme 4: Epimerization of spirolactams 12m,n.

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Scheme 5: The Dess–Martin oxidation of lactams 12l–o. Conditions: a) DMP (1.3 equiv), t-BuOH (10 mol %), CH₂Cl...

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Scheme 6: Selected transformations of the lactams trans-12b and 12o.

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Scheme 7: Diastereoselectivity for the formation of α-(aminoxy)amides 9i–k.

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Scheme 8: Rationalization of the diastereoselectivity for the formation of the α-(aminoxy)amide 9l.

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Scheme 9: Rationalization of the thermal radical cyclization diastereoselectivity of alkoxyamines 9a–k. (S)-C...

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Scheme 10: The stereochemical course for the formation of products 12m,n by thermal radical cyclization of alk...

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Scheme 11: Formation of bicycles 12o,p.

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Full Research Paper

Published 09 Mar 2021

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Pyrrolidine nucleotide analogs with a tunable conformation

Lenka Poštová Slavětínská,
Dominik Rejman and
Radek Pohl

Beilstein J. Org. Chem. 2014, 10, 1967–1980, doi:10.3762/bjoc.10.205

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Figure 1: Examples of biologically active acyclic and cyclic nucleotide analogs.

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Figure 2: The pyrrolidine nucleotide analogs investigated in this study.

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Scheme 1: The synthesis of pyrrolidine nucleotides 7–14.

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Figure 3: The numbering of the pyrrolidine ring, the nucleobase and the endocyclic phase angles for the purpo...

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Figure 4: The aliphatic part (pyrrolidine protons) of the ¹H NMR spectra of 9 measured in D₂O at different pD...

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Figure 5: Changes of selected ¹H and ¹³C chemical shifts of 9 upon pD change.

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Figure 6: The deuteration equilibria of phosphonomethyl derivatives 7–10.

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Figure 7: The aliphatic part (pyrrolidine protons) of the ¹H NMR spectra of 13 measured in D₂O at different p...

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Figure 8: Amide rotamers of phosphonoformyl derivatives 11–14.

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Figure 9: The ³¹P NMR spectra (202.3 MHz) of 14 measured (the black curve) and simulated (the red curve) at v...

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Figure 10: A part of the H,C-HSQC spectrum of derivative 13, showing the assignment of rotamers A and B.

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Figure 11: The pseudorotation pathway of the pyrrolidine ring in the compounds studied. The sign B stands for ...

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Figure 12: An example of the stereospecific assignment of pyrrolidine-ring protons of 14 in the H,H-ROESY spec...

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Figure 13: The energy profile of the five-membered pyrrolidine ring pseudorotation for adenine derivatives 9 a...

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Figure 14: The most stable conformations of adenine derivatives 9 and 13A calculated by the B3LYP/6-31++G* met...

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Full Research Paper

Published 22 Aug 2014

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