Temperature-Dependent Diastereodivergent [4 + 3] Annulation: Synthesis of Ferrocene-Fused Azepines via Rh(III) Catalysis

Temperature-Dependent Diastereodivergent [4 + 3] Annulation: Synthesis of Ferrocene-Fused Azepines via Rh(III) Catalysis

Herein, we disclose the first temperature-dependent diastereodivergent [4 + 3] annulation of ferrocene-p-tosylamides via C–H activation with allenes by a Rh catalyst. At room temperature, Rh-catalyzed [4 + 3] annulation selectively offered a kinetically controlled diastereomer [>20:1 diastereomer...

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Veröffentlicht in:Organic letters 2025-01, Vol.27 (2), p.552-558
Hauptverfasser: Thorat, Raviraj Ananda, Parganiha, Devendra, Jain, Saket, Choudhary, Vishal, Shakir, Batul, Rohilla, Komal, Jha, Raushan Kumar, Kumar, Sangit
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Sprache:eng
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Zusammenfassung:Herein, we disclose the first temperature-dependent diastereodivergent [4 + 3] annulation of ferrocene-p-tosylamides via C–H activation with allenes by a Rh catalyst. At room temperature, Rh-catalyzed [4 + 3] annulation selectively offered a kinetically controlled diastereomer [>20:1 diastereomeric ratio (dr)], whereas at 60 °C, a thermodynamically controlled diastereomer was obtained exclusively with >20:1 dr.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c03954