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-<i>p</i>-tosylamides <i>via</i> 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.

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Publication Details

Journal
Organic Letters
Published
2024-12-06
DOI
https://doi.org/10.1021/acs.orglett.4c03954
Citations
7
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.75

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article

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

Devendra Parganiha, Raviraj Ananda Thorat, Saket Jain, Sangit Kumar et al.
7 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.75
article

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

Devendra Parganiha, Raviraj Ananda Thorat, Saket Jain, Sangit Kumar, Raushan Kumar Jha, Vipin Choudhary, Batul Shakir, Komal Rohilla
article en
7 citations

Abstract

Herein, we disclose the first temperature-dependent diastereodivergent [4 + 3] annulation of ferrocene-<i>p</i>-tosylamides <i>via</i> 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.

Organic LettersVol. 27(2)
Indian Institute of Science Education and Research, Bhopal (IN)
Indian Institute of Science Education and Research Bhopal, Science and Engineering Research Board, University Grants Commission - South Eastern Regional Office
Openalex Percentile: Top 16%
Catalytic C–H Functionalization Methods
1.75
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Temperature-Dependent Diastereodivergent [4 + 3] Annulation: Synthesis of Ferrocene-Fused Azepines via Rh(III) Catalysis — Devendra Parganiha, Raviraj Ananda Thorat, et al. · Organic Letters (2024) | TGRS Research Map | TGRS