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Regioselectivities of (4+3) Cycloadditions between Furans and Oxazolidinone-Substituted Oxyallyls

  作者 LOHSE ANDREW G; KRENSKE ELIZABETH H; ANTOLINE JENNIFER E; HOUK K N; HSUNG RICHARD P  
  选自 期刊  Organic Letters;  卷期  2010年12-23;  页码  5506-5509  
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[摘要]The (4 + 3) cycloadditions of oxazolidinone-substituted oxyallyls and unsymmetrically substituted furans lead to syn regioselectivity when the furan has a 2-Me or 2-COOR substituent, while anti regioselectivity is obtained with a 3-Me or 3-COOR group. OFT calculations are performed to explain the selectivities. The reactivities and regioselectivities are consistent with the ambiphilic reactivity of amino-oxyallyls with furans.

 
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