Asymmetric Michael addition of formaldehyde N,N-dialkylhydrazones to alkylidene malonates |
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| Authors: | Vázquez Juan Prieto Auxiliadora Fernández Rosario Enders Dieter Lassaletta José M |
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| Institution: | Departamento de Química Orgánica, Universidad de Sevilla, Apdo de Correos No. 553, 41071 Seville, Spain. |
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| Abstract: | Enantiopure formaldehyde N,N-dialkylhydrazones 1 smoothly react with prochiral alkylidene malonates 2 in the presence of MgI2 to afford the corresponding Michael adducts 3 in excellent yields and good diastereoselectivities; direct racemization-free BF3.OEt2-catalyzed thiolysis of the hydrazone C=N bond affords the corresponding dithioketals 7 in optically pure or enantiomerically enriched form. |
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