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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/37879
Title: Michael addition of chiral formaldehyde N,N-dialkylhydrazones to activated cyclic alkenes
Authors: Vázquez, Juan; Cristea, Elena; Díez, Elena; Lassaletta, José M.; Prieto, María Auxiliadora; Fernández, Rosario
Keywords: N,N-dialylhydrazones
Conjugate additions
Synthetic methods
Issue Date: 10-Mar-2005
Publisher: Elsevier
Citation: Tetrahedron 61(16): 4115-4128 (2005)
Abstract: The nucleophilic conjugate addition of chiral formaldehyde N,N-dialkylhydrazones 1 to doubly activated cyclic alkenes 2–8 proceeds smoothly to afford the corresponding Michael adducts 14, 16, 18, 20, 22, 24, and 25 in variable yields and selectivities. The reactions take place either spontaneously or in the presence of MgI2 as a mild Lewis acid depending on the type of substrate. Release of the chiral auxiliary was achieved by transformation of the hydrazone moiety into acetals, dithioacetals or nitriles.
Description: 14 páginas, 1 figura, 2 tablas, 15 esquemas.
Publisher version (URL): http://dx.doi.org/10.1016/j.tet.2005.02.007
URI: http://hdl.handle.net/10261/37879
ISSN: 0040-4020
DOI: 10.1016/j.tet.2005.02.007
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