Hydration of 2-Isoxazoline Leading to a Stable 3,5,5-Trisubstituted 3-Isoxazolidinol − N-Acylated Derivatives and Ring-Chain Tautomerism Study

We have studied the cyclization of (4Z)-2,2,5,8,8-pentamethyl-4-nonene-3,7-dione (3E)-oxime (2). We have previously claimed the formation of a stable 3,5,5-trisubstituted 3-isoxazolidinol and of a bridged bicycle 4,5-dihydro-2,5-methano-1,4,3-dioxazepine in the reaction of 2 with hydrochloric acid in anhydrous diethyl ether. We report in this article that the above compounds are actually 3,3-dimethyl-1-(5Ј-tert-butyl-5Ј-hydroxy-3Ј-methylisoxazolidin-3Ј-yl)butan-2-one (5) and

show abstract

Correction to Withdrawn Article^[3,4] Cyclization Products of δ‐Oxo‐α,β‐unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether

Uncuţa

Tudose

Cãproiu

et al. 2003

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles

Yamamoto,

Matsukawa,

Kikuchi

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

The stereoselective 5-endo-trig oxygenative cyclization of α,β-unsaturated oximes was achieved using molecular oxygen (O 2 ) and a manganese catalyst. Several 4-hydroxy-4,5dihydroisoxazoles were obtained in high yields by directly incorporating O 2 from the atmosphere (eliminating the necessity for a pure oxygen environment) and using an unprecedentedly low loading of Mn(acac) 3 (as little as 0.020 mol %) without additional additives. Because of its desirable features, such as operational simplicity, inexpensive catalyst, mild reaction conditions (open flask conditions at room temperature), and broad substrate compatibility, this novel reaction provides an attractive synthetic approach to producing 4-hydroxy-4,5-dihydroisoxazoles.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Hydration of 2-Isoxazoline Leading to a Stable 3,5,5-Trisubstituted 3-Isoxazolidinol − N-Acylated Derivatives and Ring-Chain Tautomerism Study

Cited by 2 publications

References 5 publications

Correction to Withdrawn Article^[3,4] Cyclization Products of δ‐Oxo‐α,β‐unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether

Correction to Withdrawn Article^[3,4] Cyclization Products of δ‐Oxo‐α,β‐unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether

Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles

Contact Info

Product

Resources

About

Hydration of 2-Isoxazoline Leading to a Stable 3,5,5-Trisubstituted 3-Isoxazolidinol − N-Acylated Derivatives and Ring-Chain Tautomerism Study

Cited by 2 publications

References 5 publications

Correction to Withdrawn Article[3,4] Cyclization Products of δ‐Oxo‐α,β‐unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether

Correction to Withdrawn Article[3,4] Cyclization Products of δ‐Oxo‐α,β‐unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether

Manganese-Catalyzed 5-Endo-trig Oxygenative Cyclization of α,β-Unsaturated Oximes under Air and Ambient Conditions for the Synthesis of 4,5-Dihydroisoxazoles

Contact Info

Product

Resources

About

Correction to Withdrawn Article^[3,4] Cyclization Products of δ‐Oxo‐α,β‐unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether

Correction to Withdrawn Article^[3,4] Cyclization Products of δ‐Oxo‐α,β‐unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether