Non-covalent interactions in the diastereoselective synthesis of <i>cis</i>-2,3-dihydrobenzofurans: experimental and computational studies

Jamis-Oliva, Omar; López, Roger; Galdámez, Antonio; Gallardo-Fuentes, Sebastián; Vilches-Herrera, Marcelo

doi:10.1039/d3ob02070c

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob02070c

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Non-covalent interactions in the diastereoselective synthesis of cis-2,3-dihydrobenzofurans: experimental and computational studies

Omar Jamis-Oliva,

Roger López,

Antonio Galdámez

et al.

Abstract: The diastereoselective synthesis of 2,3-DHBs has been previously reported via intramolecular Michael addition reaction using alkali bases such as Cs2CO3 and K2CO3. However, no systematic study has been performed to...

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Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

López,

Jamis-Oliva,

Lühr

et al. 2024

J. Org. Chem.

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The synthesis of fused benzoxepines relies on the use of complex substrates and methodologies. Herein, we report our experimental and theoretical findings about an unprecedented Rauhut−Currier-type reaction catalyzed by Cs 2 CO 3 to access these important compounds. The developed methodology avoids the use of phosphine-or amine-based catalysts and additives. The reaction can be performed under microwave irradiation and proceeds with complete chemoselectivity.

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Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

López,

Jamis-Oliva,

Lühr

et al. 2024

J. Org. Chem.

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Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates

Tan,

Zheng,

Zhang

et al. 2024

Org. Lett.

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Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between o-aminochalcones and γ-bromocrotonates has been developed. A series of cis-2,3-disubstituted indolines and cyclopropane-fused tetrahydroquinolines were obtained via two pathways with a broad substrate scope in moderate to excellent yields under transition-metal-free conditions. It is noteworthy that the γ-bromocrotonates could be used as C1 or C2 synthons by modulating the base; in particular, the γ-bromocrotonates were used as both nucleophiles and electrophiles to generate cyclopropanes for the first time.

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Non-covalent interactions in the diastereoselective synthesis of cis-2,3-dihydrobenzofurans: experimental and computational studies

Abstract: The diastereoselective synthesis of 2,3-DHBs has been previously reported via intramolecular Michael addition reaction using alkali bases such as Cs2CO3 and K2CO3. However, no systematic study has been performed to...

Cited by 2 publications

References 45 publications

Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates

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Non-covalent interactions in the diastereoselective synthesis of cis-2,3-dihydrobenzofurans: experimental and computational studies

Abstract: The diastereoselective synthesis of 2,3-DHBs has been previously reported via intramolecular Michael addition reaction using alkali bases such as Cs2CO3 and K2CO3. However, no systematic study has been performed to...

Cited by 2 publications

References 45 publications

Cs2CO3-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

Cs2CO3-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates

Contact Info

Product

Resources

About

Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives