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

Authors:Monge, David
Martín-Zamora, Eloísa
Vázquez, Juan
Alcarazo, Manuel
Álvarez, Eleuterio
Fernández, Rosario
Lassaletta, José M.
Keywords:Enantioselective, Dialkylhydrazones, Hydroxy, Carbonyl, Catalytic asymmetric
Issue Date:20-Jun-2007
Publisher:American Chemical Society
Citation:Organic Letters 9(15): 2867-2870 (2007)
Abstract:The 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.
Description:4 páginas, 2 figuras, 1 tabla, 3 esquemas.
Publisher version (URL):http://dx.doi.org/10.1021/ol071055+
Appears in Collections:(IIQ) Artículos

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