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Title

Enantioselective Conjugate Addition of N,N-Dialkylhydrazones to α-Hydroxy Enones

AuthorsMonge, David; Martín-Zamora, Eloísa; Vázquez, Juan; Alcarazo, Manuel; Álvarez, Eleuterio ; Fernández, Rosario; Lassaletta, José M.
KeywordsEnantioselective
Dialkylhydrazones
Hydroxy
Carbonyl
Catalytic asymmetric
Issue Date20-Jun-2007
PublisherAmerican Chemical Society
CitationOrganic Letters 9(15): 2867-2870 (2007)
AbstractThe activation of alpha-hydroxy enones by the Zn(OTf)2/tBuBOX catalyst enables the enantioselective conjugate addition of 1-methyleneaminopyrrolidine as a neutral d1 synthon. Experimental evidence supports a stereochemical model where a triflate ligand controls the geometry of the catalyst-substrate complex by means of a OH-OTf hydrogen bond. The synthesis of beta-cyano acids illustrates the potential of the methodology.
Description4 páginas, 2 figuras, 1 tabla, 3 esquemas.
Publisher version (URL)http://dx.doi.org/10.1021/ol071055+
URIhttp://hdl.handle.net/10261/37643
DOI10.1021/ol071055+
ISSN1523-7060
Appears in Collections:(IIQ) Artículos
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