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

…, J Vázquez, M Alcarazo, E Álvarez, R Fernández…

Index: Monge, David; Martin-Zamora, Eloisa; Vazquez, Juan; Alcarazo, Manuel; Alvarez, Eleuterio; Fernandez, Rosario; Lassaletta, Jose M. Organic Letters, 2007 , vol. 9, # 15 p. 2867 - 2870

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Citation Number: 21

Abstract

The activation of α-hydroxy enones by the Zn (OTf) 2/t BuBOX 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 β-cyano acids illustrates the potential of the methodology.