Convenient Route to Primary (Z)-Allyl Amines and Homologs |
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| Authors: | Alejandra Gerpe Mariela Bollini |
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| Affiliation: | 1. Laboratorio de Química Orgánica , Facultad de Química/Facultad de Ciencias, Universidad de la República , Montevideo, Uruguay;2. Cátedra de Química Orgánica , Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires , Buenos Aires, Argentina |
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| Abstract: | A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)-geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C = C double bond in the deprotection with hydrazine was concomitantly observed. |
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| Keywords: | (Z)-Allyl amine (Z)-homoallyl amine (Z)-pent-4-enylamine |
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