Intramolecular Nucleophilic Substitution at the C-4 Position of Functionalized Oxetanes:  A Ring Expansion for the Construction of Various Heterocycles

Bach, Thorsten; Kather, Kristian

doi:10.1021/jo961436t

Cited by 29 publications

(16 citation statements)

References 14 publications

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“…A Paterno−Buchi reaction of silyl enol ethers followed by a Mitsunobu reaction generated oxygen-, sulfur-, or nitrogencontaining precursors. 514,515 Cyclization to six-and sevenmembered heterocycles was achieved by treatment with organometallic reagents and heating. A tetrahydropyran was synthesized in 54% yield by removing a pivaloyl protecting group with MeLi in DME and then heating at reflux to promote cyclization ( Table 28, entry 1).…”

Section: Ring-opening Reactions Of Oxetanesmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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Section: Ring-opening Reactions Of Oxetanesmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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“…Ring opening at C-4 is possible by intra-or intermolecular nucleophilic attack. 13 a Irradiation time for complete conversion of the aldehyde. b The diastereomeric ratio (dr) refers to the relative configuration of the stereogenic centers C-2 and C-3 of the oxetanes 1; it was determined by integration of the appropriate 1 H NMR signals.…”

Section: Scope and Limitationsmentioning

confidence: 99%

Paternò-Büchi Reactions of Silyl Enol Ethers and Enamides

Vogt¹,

Jödicke²,

Schröder³

et al. 2009

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3-(Silyloxy)oxetanes are obtained by irradiating mixtures of aromatic aldehydes and silyl enol ethers in benzene as the solvent. The reactions occur with high simple diastereoselectivity and, when R 1 is chiral, with high facial diastereoselectivity. Under similar conditions, but in acetonitrile rather than benzene as the preferred solvent, the Paternò-Büchi reaction of N-acyl enamines (enamides) gives the corresponding protected 3-aminooxetanes. The cis-products are obtained with significant simple diastereoselectivity.

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“…Vinyloxetanes and alkynyloxetane undergo intramolecular ring‐expansion reactions to form 3,6‐dihydro‐ 2H ‐pyrans, 2,3‐dihydrofurans, and lactones . The ring‐opening reactions of oxetanes with stoichiometric amount of nucleophiles proceeded to give various alcohols such as aryl alkyl alcohols, γ‐amino alcohols, hydroperoxy alcohols, dialkylperoxy alcohols, chiral alcohols, and so on . Moreover, oxetane derivatives are used as functional monomers that can be converted to various kinds of linear, branched, and crosslinked polyoxetanes via cationic ring‐opening polymerization using catalytic amounts of Lewis acids.…”

Section: Introductionmentioning

confidence: 99%

“…15 The ringopening reactions of oxetanes with stoichiometric amount of nucleophiles proceeded to give various alcohols such as aryl alkyl alcohols, 16 γ-amino alcohols, 17 hydroperoxy alcohols, 18,19 dialkylperoxy alcohols, 20 chiral alcohols, [21][22][23] and so on. [24][25][26][27] Moreover, oxetane derivatives are used as functional monomers that can be converted to various kinds of linear, branched, and crosslinked polyoxetanes via cationic ring-opening polymerization using catalytic amounts of Lewis acids. For example, branched and hyperbranched polyoxetanes were synthesized from hydroxyl-substituted oxetanes in the presence of catalytic boron trifluoride diethyl etherate (BF 3 -Et 2 O) or trifluoromethanesulfonic acid (TfOH).…”

mentioning

confidence: 99%

Synthesis and cationic ring‐opening polymerization of oxetane monomer containing five‐membered cyclic carbonate moiety via highly chemoselective addition of CO₂

Aoyagi

Endō

2019

J. Polym. Sci. Part A: Polym. Chem.

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The bicyclic amidinium iodide effectively catalyzed the reaction of carbon dioxide and the epoxy‐containing oxetane under ordinary pressure and mild conditions with high chemoselectivity to give the corresponding oxetane monomer containing five‐membered cyclic carbonate quantitatively. The cationic ring‐opening polymerization of the obtained monomer by boron trifluoride diethyl ether proceeded to give linear polyoxetane bearing five‐membered cyclic carbonate pendant group in high yield. The molecular weight of the polyoxetane was higher than that of polyepoxide obtained by the cationic ring‐opening polymerization of epoxide monomer containing five‐membered cyclic carbonate. The cyclic carbonate functional crosslinked polyoxetanes were also synthesized by the cationic ring‐opening copolymerization of cyclic carbonate having oxetane and commercially available bisoxetane monomers. Analyses of the resulting polyoxetanes were performed by proton nuclear magnetic resonance, size exclusion chromatography, thermogravimetric analysis, and differential scanning calorimetry. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2606–2615

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Intramolecular Nucleophilic Substitution at the C-4 Position of Functionalized Oxetanes: A Ring Expansion for the Construction of Various Heterocycles

Cited by 29 publications

References 14 publications

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Paternò-Büchi Reactions of Silyl Enol Ethers and Enamides

Synthesis and cationic ring‐opening polymerization of oxetane monomer containing five‐membered cyclic carbonate moiety via highly chemoselective addition of CO₂

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Intramolecular Nucleophilic Substitution at the C-4 Position of Functionalized Oxetanes: A Ring Expansion for the Construction of Various Heterocycles

Cited by 29 publications

References 14 publications

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Paternò-Büchi Reactions of Silyl Enol Ethers and Enamides

Synthesis and cationic ring‐opening polymerization of oxetane monomer containing five‐membered cyclic carbonate moiety via highly chemoselective addition of CO2

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Product

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Synthesis and cationic ring‐opening polymerization of oxetane monomer containing five‐membered cyclic carbonate moiety via highly chemoselective addition of CO₂