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Michael addition of chiral formaldehyde N,N-dialkylhydrazones to activated cyclic alkenes

AuthorsVázquez, Juan; Cristea, Elena; Díez, Elena; Lassaletta, José M. ; Prieto, María Auxiliadora ; Fernández, Rosario
Conjugate additions
Synthetic methods
Issue Date10-Mar-2005
CitationTetrahedron 61(16): 4115-4128 (2005)
AbstractThe 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.
Description14 páginas, 1 figura, 2 tablas, 15 esquemas.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2005.02.007
Appears in Collections:(IIQ) Artículos
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