Enantioselektive Desymmetrisierung von Cyclobutanonen: Eine Schnellstraße zu molekularer Komplexität

Sietmann, Jan; Wiest, Johannes

doi:10.1002/ange.201910767

Cited by 12 publications

(4 citation statements)

References 136 publications

(87 reference statements)

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“…1 H NMR (300 MHz, CDCl 3 ) δ 7.51 (br s, 1H), 7.45-7.43 (m, 2H), 7.17-7.15 (m, 2H), 4.51-4.47 (m, 1H), 3.27-3.17 (m, 1H), 3.06-2.97 (m, 1H), 2.57-2.48 (m, 1H), 2.24-2.14 (m, 1H overlapping with s, 3H). 13…”

Section: N-(4-(2-oxocyclobutyl)phenyl)acetamide (3 F)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 8.00-7.82 (m, 1H), 7.28-7.26 (m, 1H), 4.60-4.37 (m, 1H), 2.78-2.70 (m, 1H), 2.59 (s, 1H), 2.44 (t, J = 7.4 Hz, 1H), 2.10-1.94 (m, 1H). 13…”

Section: 22-trifluoroethyl 4-(4-acetylphenyl)butanoate (4 B)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.58-7.55 (m, 2H), 7.40-7.26 (m, 7H), 4.11 (s, 2H), 2.78-2.77 (m, 2H), 2.73-2.71 (m, 2H). 13…”

Section: -(2-(benzylthio)cyclobut-1-en-1-yl)benzonitrile (5 D)mentioning

confidence: 99%

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Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Koudelka

Tobrman

2021

Eur J Org Chem

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We report a novel process for the preparation of 2-substituted cyclobutanones. Such a method relies on the cross-coupling reaction of bromocyclobutenyl diethyl phosphate with either boronic acids or organozinc reagents. Dephosphorylation of the prepared 2-substituted cyclobutenyl phosphates affords 2substituted cyclobutanones. We observed that the course of the dephosphorylation reaction depends on the properties of the substituents found on the cyclobutene nucleus. The presence of groups capable of stabilizing the negative charge is necessary for ring opening of cyclobutanones. The scope of the reported process for the preparation of 2-substituted cyclobutanones has also been extended to the preparation of cyclobutenyl sulfides.

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Section: N-(4-(2-oxocyclobutyl)phenyl)acetamide (3 F)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 8.00-7.82 (m, 1H), 7.28-7.26 (m, 1H), 4.60-4.37 (m, 1H), 2.78-2.70 (m, 1H), 2.59 (s, 1H), 2.44 (t, J = 7.4 Hz, 1H), 2.10-1.94 (m, 1H). 13…”

Section: 22-trifluoroethyl 4-(4-acetylphenyl)butanoate (4 B)mentioning

confidence: 99%

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Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Koudelka

Tobrman

2021

Eur J Org Chem

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“…Desymmetrization reactions are highly attractive manners for the rapid synthesis of optical compounds . Inspired by these works, we have designed novel substrates for the construction of the desired hydrogenated benzofuranone skeletons via a desymmetrization pathway.…”

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confidence: 99%

Desymmetrization Process by Mg(II)-Catalyzed Intramolecular Vinylogous Michael Reaction

Yang

Peng

et al. 2020

Org. Lett.

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Chiral magnesium catalyzed intramolecular vinylogous Michael reaction of novel cyclohexadienones via a desymmetrization process is reported. (R)-BINOL derived ligand and an achiral amide were employed in the current in situ generated magnesium catalyst, giving the corresponding hydrogenated benzofuranone skeletons in good to excellent enantioselectivities with high yields. This simple and efficient strategy could be utilized for the synthesis of aromatized α,β-unsaturated ester and Br-substituted hydrogenated benzofuranone in good yields under mild conditions. Letter pubs.acs.org/OrgLett

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Desymmetrisierung von prochiralen Cyclobutanonen via Stickstoffinsertion: Ein einfacher Zugang zu chiralen γ‐Lactamen

et al. 2021

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Die asymmetrische Synthese von γ‐Lactamen wird über die Cyclobutanon‐Ringerweiterung unter Verwendung von (1S,2R)‐1‐Amino‐2‐Indanol zur chiralen Induktion erreicht. Die mechanistische Analyse der entscheidenden N,O‐Ketal‐Umlagerung zeigt ein Curtin‐Hammett‐Szenario, das eine späte Stereoinduktion (bis zu 88:12 dr) ermöglicht und durch spektroskopische, kristallographische und rechnerische Untersuchungen bestätigt wird. In Kombination mit einem einfachen Entschützungsverfahren ermöglicht diese operativ einfache Sequenz die Synthese enantiomerenreiner γ‐Lactame, einschließlich solcher, die quartäre Stereozentren mit ausschließlich Kohlenstoffatomen tragen. Darüber hinaus demonstriert die formale Synthese der Wirkstoffe Baclofen, Brivaracetam und Pregabalin den präparativen Nutzen und unterstreicht die allgemeine Anwendbarkeit der vorgestellten Methode.

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Enantioselektive Desymmetrisierung von Cyclobutanonen: Eine Schnellstraße zu molekularer Komplexität

Cited by 12 publications

References 136 publications

Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Desymmetrization Process by Mg(II)-Catalyzed Intramolecular Vinylogous Michael Reaction

Desymmetrisierung von prochiralen Cyclobutanonen via Stickstoffinsertion: Ein einfacher Zugang zu chiralen γ‐Lactamen

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