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A Formal [4+4] Complementary Ambiphile Pairing Reaction: A New Cyclization Pathway for ortho-Quinone Methides

  作者 SAMARAKOON THIWANKA B; HUR MOON Y; KURTZ RYAN D; HANSON PAUL R  
  选自 期刊  Organic Letters;  卷期  2010年12-10;  页码  2182-2185  
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[摘要]A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.

 
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