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Catalytic Asymmetric 6 pi-Electrocyclization: Accessing Highly Substituted Optically Active 2-Pyrazolines via Diastereoselective Alkylations

  作者 MUELLER STEFFEN; LIST BENJAMIN  
  选自 期刊  Synthesis;  卷期  2010年-13;  页码  2171-2178  
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[摘要]The chiral phosphoric acid catalyzed asymmetric electrocyclization of alpha,beta-unsaturated hydrazones has been studied. This reaction is one of the first catalytic asymmetric 6 pi-electrocyclizations reported, and enables the synthesis of 2-pyrazolines in high yields and enantiomeric ratios. The obtained products are not only interesting because of their pharmaceutical properties, but can be manipulated in highly diastereoselective fashion, as shown for alkylation reactions. Thus, the combination of catalytic asymmetric 6 pi-electrocyclization followed by diastereoselective alkylation can provide interesting synthetic building blocks in optically active form.

 
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