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

Herein, we disclose the first temperature-dependent diastereodivergent\n[4 + 3] annulation of ferrocene-<i>p</i>-tosylamides <i>via</i> C–H activation with allenes by a Rh catalyst.\nAt room temperature, Rh-catalyzed [4 + 3] annulation selectively offered\na kinetically controlled diastereomer [>20:1 diastereomeric ratio\n(dr)], whereas at 60 °C, a thermodynamically controlled diastereomer\nwas obtained exclusively with >20:1 dr.

Publication Details

Journal
Figshare
Published
2024-12-06
DOI
https://doi.org/10.1021/acs.orglett.4c03954.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

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

Figshare
Mycorrhizal Fungi and Plant Interactions
article

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

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Abstract

Herein, we disclose the first temperature-dependent diastereodivergent\n[4 + 3] annulation of ferrocene-<i>p</i>-tosylamides <i>via</i> C–H activation with allenes by a Rh catalyst.\nAt room temperature, Rh-catalyzed [4 + 3] annulation selectively offered\na kinetically controlled diastereomer [>20:1 diastereomeric ratio\n(dr)], whereas at 60 °C, a thermodynamically controlled diastereomer\nwas obtained exclusively with >20:1 dr.

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Temperature-Dependent\nDiastereodivergent [4 + 3] Annulation:\nSynthesis of Ferrocene-Fused Azepines via Rh(III) Catalysis · Figshare (2024) | TGRS Research Map | TGRS