Abstract
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
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