Intramolecular 1,3-dipolar cycloaddition reaction of novel 2-azetidinone-tethered alkenyl nitrile oxides

Alcaide, Benito; Almendros, Pedro; Sáez, Estéban

doi:10.3998/ark.5550190.0005.416

Cited by 10 publications

References 3 publications

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Synthesis of 4,5‐Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic System

Cecchi

Sarlo

Machetti

2008

Chemistry A European J

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A new procedure for the synthesis of 4.5-dihydroisoxazoles by condensation of primary nitro compounds with olefins by using a copper/base catalytic system is described. The catalytic effect of copper(II) salts is evidenced by comparison of the reaction rates. Thus, activated nitro compounds react faster than with organic catalysis by tertiary amines, whereas nitroalkanes, unable to condense with dipolarophiles in the presence of the base alone, undergo the reaction on addition of a copper(II) catalyst. The observed occurrence of induction periods in most reactions is ascribed to an equilibrium preceding the rate-determining step, and gives a hint as to the proposed reaction mechanism. The results indicate that this method might be of practical and general utility for synthetic practice.

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Synthesis of 4,5‐Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic System

Cecchi

Sarlo

Machetti

2008

Chemistry A European J

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Diastereoselective Route to Novel Fused or Bridged Tricyclic β‐Lactams through Intramolecular Nitrone–Alkene Cycloaddition of 2‐Azetidinone‐Tethered Alkenylaldehydes – Synthetic Applications to Carbacephams and Cyclic β‐Amino Acid Derivatives

Alcaide

Sáez

2005

Eur J Org Chem

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A convenient, regio-and stereoselective direct route to optically pure unusually fused or bridged tricyclic β-lactams has been developed by use of intramolecular nitrone-alkene cycloaddition (INAC) reactions of easily available monocyclic 2-azetidinone-tethered alkenylaldehydes as the key synthetic step. The regioselectivity of the cycloaddition can be tuned by moving the alkene substituent from N1 to C3 on the 2-azetidinone ring. In addition, some simple, interesting transformations were tested on representative examples of

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A Simple and Efficient One‐Pot Synthesis of 3‐Acylisoxazolines from Alcohols and α‐Nitro Ketones in the Presence of NaHSO₄/SiO₂

et al. 2018

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A simple and efficient method for the synthesis of 3‐acylisoxazolines has been developed using alcohols and α‐nitro ketones in the presence of NaHSO4/SiO2. The alcohols and α‐nitro ketones are initially converted into alkenes and nitrile oxides, respectively, and then react with one another to give 3‐acylisoxazolines. This procedure, using alcohols, gave the desired dihydroisoxazoles more effectively than the conventional procedure using alkenes as starting materials. The reaction proceeded through three pathways depending on the type of alcohol used; reactions between nitrile oxides and (I) endo and exo alkenes, (II) dimerized alkenes and (III) single alkenes. Most of the reactions proceeded efficiently and gave the corresponding 3‐acylisoxazolines in good to excellent yield.

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Intramolecular 1,3-dipolar cycloaddition reaction of novel 2-azetidinone-tethered alkenyl nitrile oxides

Cited by 10 publications

References 3 publications

Synthesis of 4,5‐Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic System

Synthesis of 4,5‐Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic System

Diastereoselective Route to Novel Fused or Bridged Tricyclic β‐Lactams through Intramolecular Nitrone–Alkene Cycloaddition of 2‐Azetidinone‐Tethered Alkenylaldehydes – Synthetic Applications to Carbacephams and Cyclic β‐Amino Acid Derivatives

A Simple and Efficient One‐Pot Synthesis of 3‐Acylisoxazolines from Alcohols and α‐Nitro Ketones in the Presence of NaHSO₄/SiO₂

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Intramolecular 1,3-dipolar cycloaddition reaction of novel 2-azetidinone-tethered alkenyl nitrile oxides

Cited by 10 publications

References 3 publications

Synthesis of 4,5‐Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic System

Synthesis of 4,5‐Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic System

Diastereoselective Route to Novel Fused or Bridged Tricyclic β‐Lactams through Intramolecular Nitrone–Alkene Cycloaddition of 2‐Azetidinone‐Tethered Alkenylaldehydes – Synthetic Applications to Carbacephams and Cyclic β‐Amino Acid Derivatives

A Simple and Efficient One‐Pot Synthesis of 3‐Acylisoxazolines from Alcohols and α‐Nitro Ketones in the Presence of NaHSO4/SiO2

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A Simple and Efficient One‐Pot Synthesis of 3‐Acylisoxazolines from Alcohols and α‐Nitro Ketones in the Presence of NaHSO₄/SiO₂