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Highly Selective a-Acylvinyl Anion Additions to Imines.

  作者 Reynolds, Troy E.;Binkley, Michael S.;Scheidt, Karl A.;  
  选自 期刊  Organic Letters;  卷期  2008年10-22;  页码  5227-5230  
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[摘要]a-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting a-acylvinyl anion equiv. undergo highly selective addns. to N-tert-butanesulfinyl imines generating b-substituted aza-Morita-Baylis-Hillman-type (aza-MBH) products. High yields are achieved for a wide range of a-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/? minor) favoring the Z-isomer of the alkene.

 
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