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Periselectivity Switch of Acylketenes in Cycloadditions with 1-Azadienes: Microwave-Assisted Diastereoselective Domino Three-Component Synthesis of alpha-Spiro-delta-lactams

  作者 PRESSET MARC; COQUEREL YOANN; RODRIGUEZ JEAN  
  选自 期刊  Organic Letters;  卷期  2010年12-18;  页码  4212-4215  
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[摘要]The microwave-assisted Wolff rearrangement of cyclic 2-diazo-1,3-diketones in the presence of primary amines and alpha beta-unsaturated aldehydes provides a straightforward three-component stereoselective access to a variety of alpha-spiro-beta-lactams following an imination/Wolff rearrangement/[2 + 4] cycloaddition domino sequence. With aniline derivatives, a complementary aza-Wittig/Wolff rearrangement/[2 + 4] sequence was developed. These reactions feature an unprecedented reactivity of acylketenes as dienophiles in 6 pi electrocyclic processes.

 
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