The synthesis and Diels–Alder reactions of 2-prop-2-enylidene-1,3-dioxolan

We report the cycloaddition reactions of 1-alkoxy-1amino-1,3-butadienes. These doubly activated dienes are prepared on a multigram scale from crotonic acid chloride and its derivatives. The dienes undergo Diels−Alder (DA) and hetero-Diels−Alder (HDA) reactions under mild reaction conditions with a variety of electrondeficient dienophiles to afford cycloadducts in good yields with excellent regioselectivities. The hydrolysis of the DA cycloadducts provides 6-substituted and 6,6-disubstituted 2-cylohexenones, which are versatile building blocks for complex molecule synthesis. The corresponding HDA cycloadducts afford 6-substituted 5,6-dihydropyran-2-ones.

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.

The synthesis and Diels–Alder reactions of 2-prop-2-enylidene-1,3-dioxolan

Cited by 4 publications

References 1 publication

ChemInform Abstract: THE SYNTHESIS AND DIELS‐ALDER REACTIONS OF 2‐PROP‐2‐ENYLIDENE‐1,3‐DIOXOLANE

ChemInform Abstract: THE SYNTHESIS AND DIELS‐ALDER REACTIONS OF 2‐PROP‐2‐ENYLIDENE‐1,3‐DIOXOLANE

Synthesis and reactions of achiral 3-substituted vinylketene acetals as dienes in the Diels-Alder reaction

Diels–Alder Reactions of 1-Alkoxy-1-amino-1,3-butadienes: Direct Synthesis of 6-Substituted and 6,6-Disubstituted 2-Cyclohexenones and 6-Substituted 5,6-Dihydropyran-2-ones

Contact Info

Product

Resources

About