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Sequential Organocatalyzed Michael Addition/[3 + 2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids.

  作者 Bonne, Damien;Salat, Lydie;Dulcere, Jean-Pierre;Rodriguez, Jean;  
  选自 期刊  Organic Letters;  卷期  2008年10-23;  页码  5409-5412  
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[摘要]An asym. synthesis of functionalized cyclopentanoids bearing up to four stereogenic centers from easily accessible nitroalkenes and unsatd. aldehydes are described. The overall sequence includes an enantioselective organocatalytic Michael addn. and a intramol. [3 + 2]-heterocyclization between an in situ generated silylnitronate and the unactivated double bond. Finally, the fused isoxazoline can be further transformed to various cyclopentanoids.

 
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