2024-03-28T12:53:59Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/295402020-05-14T09:50:28Zcom_10261_33com_10261_5col_10261_286
Metal-Catalyzed Cycloisomerization and Tandem Oxycyclization/Hydroxylation of Alkynols: Synthesis of Nonfused, Spiranic and Fused Oxabicyclic β-Lactams
Alcaide, Benito
Almendros, Pedro
Martínez del Campo, Teresa
Carrascosa, Rocío
Alkynes
Cyclization
Gold
Lactams
Platinum
8 páginas, 11 esquemas. El documento en word es el artículo post-print.
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 PtII or AuIII salts, cyclization reactions occurred preferentially through a tandem oxycyclization/hydroxylation of alkynols to afford a variety of nonfused, spiranic and fused oxabicyclic β-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.
2010-11-25T14:37:37Z
2010-11-25T14:37:37Z
2010-09
artículo
European Journal of Organic Chemistry 2010(5): 4912-4919 (2010)
1434-193X
http://hdl.handle.net/10261/29540
10.1002/ejoc.201000710
eng
http://dx.doi.org/10.1002/ejoc.201000710
openAccess
Wiley-VCH