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Title

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

AuthorsAlcaide, Benito ; Almendros, Pedro ; Martínez del Campo, Teresa; Carrascosa, Rocío
KeywordsAlkynes
Cyclization
Gold
Lactams
Platinum
Issue DateSep-2010
PublisherWiley-VCH
CitationEuropean Journal of Organic Chemistry 2010(5): 4912-4919 (2010)
Abstract2-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.
Description8 páginas, 11 esquemas. El documento en word es el artículo post-print.
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.201000710
URIhttp://hdl.handle.net/10261/29540
DOI10.1002/ejoc.201000710
ISSN1434-193X
Appears in Collections:(IQOG) Artículos
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