Radical Zinc-Atom Transfer Based Multicomponent Approaches to 3-Alkylidene-Substituted Tetrahydrofurans

Autor:	Fabrice Chemla, Max P. Nüllen, Florian Dulong, Franck Ferreira, Alejandro Perez-Luna
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Cascade reaction Chemistry Metalation Radical Organic Chemistry Electrophile Alkyne Stereoselectivity Zinc atom Medicinal chemistry Catalysis Alkyl
Zdroj:	Synthesis. 2011:1347-1360
ISSN:	1437-210X 0039-7881
Popis:	A domino 1,4-addition/alkyne carbozincation sequence basedon a radical zinc-atom transfer process is disclosed. Two efficientmulticomponent approaches to 3-alkylidenetetrahydrofurans from β-(propargyloxy)enoatesbearing pendant alkynes (including ynamides) have been established:one involving the direct addition of dialkylzincs, and the secondinvolving the dimethylzinc-mediated addition of alkyl iodides. Bothsequences utilize the stereoselective formation of intermediatealkylidenezincs well suited for in situ functionalizationwith electrophiles. 1 Introduction 2 1,4-Addition/Cyclization of Dialkylzincs on β-(Propargyl-oxy)enoates 2.1 β-(Propargyloxy)enoates with a Pendant TerminalAlkyne 2.2 β-(Propargyloxy)enoates with a Pendant Substituted Alkyne 2.3 β-(Propargyloxy)enoates with a Pendant Ynamide 3 1,4-Addition/Cyclization of Alkylzinc Halides on β-(Propargyloxy)enoates 4 Dialkylzinc-Mediated 1,4-Addition/Cyclization ofAlkyl Iodides on β-(Propargyloxy)enoates 5 Conclusion; Current and Future Work
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3733f031226d3bb381795bec62a0e358 https://doi.org/10.1055/s-0030-1259993 Zobrazit plný text záznamu