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Synlett 2001; 2001(6): 0872-0874
DOI: 10.1055/s-2001-14597
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Carbohydrate to Carbocycle Conversions via Intramolecular Propargylation with Et2Zn/Pd(0)/Yb(OTf)3

José M. Aurrecoechea* , Mónica Arrate, Beatriz López
  • *Departamento de Química Orgánica II, Facultad de Ciencias, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain; Fax 34-94 464 8500; E-mail: qopaufem@lg.ehu.es
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Publication Date:
31 December 2001 (online)

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Carbohydrate-derived propargylic esters react with Et2Zn and catalytic Pd(0), in the presence of a Lewis acid, to generate nucleophilic allenyl metal species capable of intramolecular addition to a tethered carbonyl group. This results in the formation of enantiomerically pure functionalized cyclopentanes with high stereoselectivity and in preparatively useful yields. A high preference is observed for a trans relationship between the alkynyl and OH groups in the cyclopentane products, implying that the cyclization proceeds through open transition states.

carbohydrates - carbocycles - cyclizations - palladium - zinc