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Metal-Catalyzed Cycloisomerization and Tandem Oxycyclization/Hydroxylation of Alkynols: Synthesis of Nonfused, Spiranic and Fused Oxabicyclic beta-Lactams

  作者 ALCAIDE BENITO; ALMENDROS PEDRO; MARTINEZ DEL CAMPO TERESA; CARRASCOSA ROCIO  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-25;  页码  4912-4919  
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[摘要]2-Azetidinone-tethered alkynols, readily prepared from the corresponding aldehydes or ketones, were used as starting materials for the oxycyclization reaction catalyzed by precious metals. AgOAc exclusively affords dihydrofurans, methylenetetrahydrofurans, or methylenetetrahydro-2H-pyrans through specific 5-endo, 5-exo, or 6-exo pathways, respectively. Interestingly, in the presence of a catalytic amount of Pt-II or Au-III salts, cyclization reactions occurred preferentially through a tandem oxycyclization/hydroxylation of alkynols to afford a variety of nonfused, spiranic and fused oxabicyclic beta-lactams in moderate to high yields. Besides, it has been observed that the tandem gold-catalyzed cycloetherification/hydroxylation of a methoxymethyl alkynyl ether can be accomplished.

 
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