Synthesis and Diels-Alder Reactions of a New Kind of Chiral Dienophiles: Cyclic Vinyl-p-tolylsulfilimines

Autor:	Lorena González Gutiérrez, José L. García Ruano, Ana M. Martín Castro, Jesús H. Rodríguez Ramos,† and, Francisco Yuste, Antonio Esteban Gamboa
Rok vydání:	2000
Předmět:	chemistry.chemical_classification Cyclopentadiene Double bond Chemistry Organic Chemistry Sulfilimine Biochemistry Medicinal chemistry Catalysis Adduct chemistry.chemical_compound Moiety Reactivity (chemistry) Methanol Physical and Theoretical Chemistry
Zdroj:	Organic letters. 2(6)
ISSN:	1523-7052
Popis:	A new kind of chiral dienophiles, cyclic vinyl-p-tolylsulfilimines (2a and 2b), were obtained from the corresponding (Z)-sulfinylacrylonitriles with HBF(4) and methanol. The asymmetric Diels-Alder reaction of optically pure 2a with cyclopentadiene under mild thermal or catalyzed conditions afforded only the endo-4a adduct with complete endo and pi-facial selectivities. The ability of the sulfilimine moiety to enhance the dienophilic reactivity of the double bond is similar to that of the sulfinyl group.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0820ba69ecee44ddf88a7939dfbc1138 https://pubmed.ncbi.nlm.nih.gov/10814422 Zobrazit plný text záznamu