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Organocatalytic Domino Double Michael Reaction of Ethyl (E)-7-Oxohept-2-enoate and alpha,beta-Unsaturated Aldehydes: Efficient Asymmetric Synthesis of Cyclohexanes with Four Contiguous Stereocenters

  作者 HONG BORCHERNG; SADANI AMIT A; NIMJE ROSHAN Y; DANGE NITIN S; LEE GENEHSIANG  
  选自 期刊  Synthesis;  卷期  2011年-12;  页码  1887-1895  
  关联知识点  
 

[摘要]Organocatalytic domino double Michael reactions of ethyl (E)-7-oxohept-2-enoate and alpha,beta-unsaturated aldehydes provided ethyl 2-(2,4-diformyl-3-phenylcyclohexyl)acetate with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (>99% ee). The adducts were further transformed to octahydro-3H-2-benzopyran-3-ones, octahydroisoquinolin-3(2H)-ones, and decahydro-5H-oxazolo[2,3-a]isoquinolin-5-ones.

 
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