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

  作者 CHEMLA FABRICE; DULONG FLORIAN; FERREIRA FRANCK; NUELLEN MAX P; PEREZLUNA ALEJANDRO  
  选自 期刊  Synthesis;  卷期  2011年-9;  页码  1347-1360  
  关联知识点  
 

[摘要]A domino 1,4-addition/alkyne carbozincation sequence based on a radical zinc-atom transfer process is disclosed. Two efficient multicomponent approaches to 3-alkylidenetetrahydrofurans from beta-(propargyloxy)enoates bearing pendant alkynes (including ynamides) have been established: one involving the direct addition of dialkylzincs, and the second involving the dimethylzinc-mediated addition of alkyl iodides. Both sequences utilize the stereoselective formation of intermediate alkylidenezincs well suited for in situ functionalization with electrophiles.

 
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