Synthesis of α-Hydroxyhydrazones from Aldehydes

Rosario Fernández; Eloísa Martín-Zamora; Carmen Pareja; Manuel Alcarazo; Jesús Martín; JoséM. Lassaletta

doi:10.1055/s-2001-15139

Synlett 2001; 2001(7): 1158-1160
DOI: 10.1055/s-2001-15139

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Synthesis of α-Hydroxyhydrazones from Aldehydes

Rosario Fernández^* , Eloísa Martín-Zamora, Carmen Pareja, Manuel Alcarazo, Jesús Martín, José M. Lassaletta

^*Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado de Correos No. 553, E-41071, Seville, Spain; Fax + 34 9 54 46 05 65; E-mail: jmlassa@cica.es

Abstract

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The 1,2-addition of formaldehyde N,N-dialkylhydrazones to simple aldehydes takes place in the presence of ZnCl₂ or Et₂AlCl to afford the corresponding α-hydroxyhydrazones. More reactive aldehydes undergo addition of these reagents in the absence of promoters. Use of (S)-1-methyleneamino-2-(diphenylmethoxymethyl) pyrrolidine as the reagent afforded separable mixtures of diastereoisomers, thereby allowing for the isolation of optically pure adducts in a single step.

diastereoselectivity - hydroxyhydrazones - nucleophilic addition

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