ChemInform Abstract: BF<sub>3</sub>‐Mediated cis‐Selective Cycloaddition of O‐Silyloxime with Alkenes.

Morita, Nobuyoshi; Kono, Rina; Fukui, Kenji; Miyazawa, Asuka; Masu, Hyuma; Azumaya, Isao; Ban, Shurong; Hashimoto, Yoshimitsu; Okamoto, Iwao; Tamura, Osamu

doi:10.1002/chin.201539124

Cited by 2 publications

(2 citation statements)

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“…Several reduction reagents were used depending on the substrate. Tran et al 230 and Chakrabarty et al 231 choose Zn/AcOH, while Morita et al 232 preferred Mo(CO) 6 .…”

Section: From Ring Opening Of Isoxazolidines To Novel Heterocyclesmentioning

confidence: 99%

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

et al. 2016

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The isoxazolidine ring represents one of the privileged structures in medicinal chemistry, and there have been an increasing number of studies on isoxazolidine and isoxazolidine-containing compounds. Optimization of the 1,3-dipolar cycloaddition (1,3-DC), original methods including electrophilic or palladium-mediated cyclization of unsaturated hydroxylamine, has been developed to obtain isoxazolidines. Novel reactions involving the isoxazolidine ring have been highlighted to accomplish total synthesis or to obtain bioactive compounds, one of the most significant examples being probably the thermic ring contraction applied to the total synthesis of (±)-Gelsemoxonine. The unique isoxazolidine scaffold also exhibits an impressive potential as a mimic of nucleosides, carbohydrates, PNA, amino acids, and steroid analogs. This review aims to be a comprehensive and general summary of the different isoxazolidine syntheses, their use as starting building blocks for the preparation of natural compounds, and their main biological activities.

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“…Several reduction reagents were used depending on the substrate. Tran et al 230 and Chakrabarty et al 231 choose Zn/AcOH, while Morita et al 232 preferred Mo(CO) 6 .…”

Section: From Ring Opening Of Isoxazolidines To Novel Heterocyclesmentioning

confidence: 99%

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

et al. 2016

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“…Instead, a rearrangement cascade takes place and a racemic mixture of compound 6c is formed. Hereby, we assume that the actual product 4a is formed, but immediately BF 3 induces a Si−Si bond cleavage, resulting in the formation of a fluoroacylsilane as well as a silenolate (a), 26 which subsequently undergo an intermolecular sila-aldol reaction (b). In the presence of MeOH, this aldol product is protonated to the corresponding alcohol (c).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of a Variety of α,ω-Bisacylpolysilanes─A Study on Reactivity and Accessibility

et al. 2022

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In this study, a variety of α,ω-bisacylpolysilanes were synthesized via two synthetic protocols. The first method for obtaining these compounds is based on the substitution reaction of bromine either on silica gel or by the use of silver salts. Surprisingly, instead of the expected bromine substitution product PhC(O)(SiMe2)2C(O)Ph 4a, we found the formation of the diastereomer PhC(O)(SiMe2)2CBrPhOCBrPh(SiMe2)2C(O)Ph 4b indicating a more complex reaction cascade. On the other hand, the phenylated compound 3b yielded the expected bromine substitution product PhC(O)(SiPh2)2C(O)Ph 4c. For the second protocol, we utilized the Corey–Seebach approach to isolate other representatives of this compound class. We found that the substituents at the α-silicon atoms influence the selectivity of the dethioketalization. While the ethylated and phenylated disilanes 5b,c yield the expected bisacyldisilanes 6a,b, the methylated disilane 4a undergoes a BF3-induced Si–Si bond breakage followed by an intermolecular sila-aldol reaction. This hitherto unknown sila-aldol reaction results in the formation of the enantiomer PhC(O)SiMe2C(OMe)PhSiMe2F 6c in excellent yields. All isolated compounds were analyzed by a combination of NMR spectroscopy, ultraviolet–visible (UV–vis) spectroscopy, single-crystal X-ray crystallography, and mass spectrometry. Furthermore, the photochemical pathways of two representative examples (4b,c) were examined.

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ChemInform Abstract: BF₃‐Mediated cis‐Selective Cycloaddition of O‐Silyloxime with Alkenes.

Cited by 2 publications

References 1 publication

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Synthesis and Characterization of a Variety of α,ω-Bisacylpolysilanes─A Study on Reactivity and Accessibility

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ChemInform Abstract: BF3‐Mediated cis‐Selective Cycloaddition of O‐Silyloxime with Alkenes.

Cited by 2 publications

References 1 publication

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Synthesis and Characterization of a Variety of α,ω-Bisacylpolysilanes─A Study on Reactivity and Accessibility

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ChemInform Abstract: BF₃‐Mediated cis‐Selective Cycloaddition of O‐Silyloxime with Alkenes.