Additive-free regio- and diastereoselective construction of fully-substituted isoxazolidines employing diazo compounds

Gupta, Ekta; Zaheer, Mohd Khalid; Kant, Ravi; Mohanan, Kishor

doi:10.1039/c8qo01421c

Cited by 25 publications

(13 citation statements)

References 52 publications

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“…To address this limitation, our group reported the additive-free three-component synthesis of phosphonylated isoxazolidines 35 via the [3 + 2] cycloaddition reaction between allenoates 34 and nitrone generated in situ from Seyferth-Gilbert reagent 1 and nitrosoarenes 33. [35] A brief optimization of the reaction conditions revealed that nitrosobenzene reacts with Seyferth-Gilbert reagent and γmethyl allenoate in CH 3 CN at 50°C to furnish the phosphonylated isoxazolidine in the highest yield. Under the optimized reaction conditions, we set to examine the substrate scope for the protocol (Scheme 22).…”

Section: Synthesis Of Isoxazolidinesmentioning

confidence: 99%

“…However, the formation of nitrones was limited, owing to the need for an additional step for its preparation. To address this limitation, our group reported the additive‐free three‐component synthesis of phosphonylated isoxazolidines 35 via the [3+2] cycloaddition reaction between allenoates 34 and nitrone generated in situ from Seyferth‐Gilbert reagent 1 and nitrosoarenes 33 [35] …”

Section: Synthesis Of Isoxazolidinesmentioning

confidence: 99%

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The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Jamali

Vaishanv

Mohanan

2020

The Chemical Record

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Azaheterocycles are one of the most prevalent classes of compounds present in numerous bioactive compounds, natural products, and agrochemicals, and undoubtedly, new methods to access them are always in high demand. Among the methods available, the 1,3dipolar cycloaddition reactions involving diazo compounds are particularly attractive because of their ability to rapidly construct densely functionalized azaheterocycles in a regioselective manner. In this context, the Bestmann-Ohira reagent has become a well-known reagent for the 1,3dipolar cycloaddition reactions to produce phosphonylated heterocycles, besides its widespread use as a homologating agent for the conversion of aldehydes to alkynes. This account details our efforts toward broadening the synthetic utility of the Bestmann-Ohira reagent and related compounds for the preparation of azaheterocycles such as pyrazoles, spirooxindoles, triazoles, triazolines, and spiropyrazolines, emphasizing on domino multicomponent reactions employing readily available feedstock reagents.

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Section: Synthesis Of Isoxazolidinesmentioning

confidence: 99%

Section: Synthesis Of Isoxazolidinesmentioning

confidence: 99%

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Jamali

Vaishanv

Mohanan

2020

The Chemical Record

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“…The scope of trifluoromethylnitrone 51 was subsequently explored in [3 + 2]‐cycloaddition with allenic esters 6 in 2019 (Scheme 28) [50]. This three‐component protocol afforded trifluoromethylated isoxazolidines 58 in high yields.…”

Section: Application Of Trifluorodiazoethane In Cf3‐heterocyclesmentioning

confidence: 99%

“…In 2018, our group developed an effective and general three-component reaction to synthesize trifluoromethylated spiro-isoxazolidine-oxindoles 56 (Scheme 27) [49]. The method utilized a [3 + 2]cycloaddition reaction of phenacylideneoxindoles 55 with trifluoromethylnitrone 51, generated in situ from The scope of trifluoromethylnitrone 51 was subsequently explored in [3 + 2]-cycloaddition with allenic esters 6 in 2019 (Scheme 28) [50]. This three-component protocol afforded trifluoromethylated isoxazolidines 58 in high yields.…”

Section: Synthesis Of Cf 3 -Substituted Isoxazolidines Oxazolines Iso...mentioning

confidence: 99%

Trifluorodiazoethane: A versatile building block to access trifluoromethylated heterocycles

Kumar

Khan

Ahamad

et al. 2021

Journal of Heterocyclic Chem

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Trifluoromethylated heterocycles have attracted remarkable interest in the last decades. The beneficial physicochemical and biological properties imparted by the incorporation of trifluoromethyl group into heterocycles have been the key factors to the frequent occurrence of trifluoromethyl group in several heterocycles of pharmaceutical and agrochemical relevance. In consequence, the construction of this class of compounds has become a major subject of research in recent years. In this context, 2,2,2-trifluorodiazoethane (CF 3 CHN 2 ) has emerged as an important reagent in the synthesis of trifluoromethylated heterocycles, thanks to the versatility of this reagent in undergoing a multitude of synthetic transformations. CF 3 CHN 2 readily participates in [2 + 1]-, [3 + 2]-, and [3 + 3]-cycloaddition reactions, as a trifluoromethyl-containing dipole, thereby creating new approaches to trifluoromethylated heterocycles. The last decade has witnessed phenomenal growth in this area, and now, several methods are available to access highly functionalized 5-and 6-membered trifluoromethyl-containing heterocycles. In this review, we aim to demonstrate the use of CF 3 CHN 2 in the preparation of different classes of CF 3 -substituted heterocycles, giving emphasis to the past 10 years.

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“…Alternatively, diazo compounds undergoing the noncarbenoid-type intermediate process can also been used for three-component reaction. For example, three-component reactions involving diazo compounds and nirosoarenes are well developed, in which nitrone intermediates would be formed initially with diazo compounds used as noncarbenoid-type nucleophiles, and participate in 1,3-dipolar cycloaddition with alkenes or alkynes to produce isoxazolidines or aziridines, respectively. However, the related asymmetric example is rare.…”

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confidence: 99%

Asymmetric Catalytic Synthesis of Epoxides via Three-Component Reaction of Diazoacetates, 2-Oxo-3-ynoates, and Nitrosoarenes

et al. 2020

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An enantioselective three-component reaction of diazoacetates, 2-oxo-3-ynoates, and nitrosoarenes has been developed by using a chiral N,N′-dioxide/Ni(OTf) 2 complex. This catalytic manifold allows rapid access to a series of multifunctional chiral epoxides containing an imino ketone substituent in moderate to good yields (up to 82%) and excellent diastereo-and enantioselectivities (up to >95/5 dr and 99% ee) with high levels of Z/E ratios (up to >95/5 Z/E) under mild reaction conditions.

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Additive-free regio- and diastereoselective construction of fully-substituted isoxazolidines employing diazo compounds

Abstract: An efficient additive-free three-component access to densely functionalized isoxazolidines using diazo compounds, nitrosoarene, and allenic esters has been uncovered.

Cited by 25 publications

References 52 publications

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Trifluorodiazoethane: A versatile building block to access trifluoromethylated heterocycles

Asymmetric Catalytic Synthesis of Epoxides via Three-Component Reaction of Diazoacetates, 2-Oxo-3-ynoates, and Nitrosoarenes

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