Preparation of 1-ferrocenyl-2-methyl-1-propylamine,a highly effective chiral template in asymmetrically induced synthesis |
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Authors: | Gerhard Eberle Inger Lagerlund Ivar Ugi Reinhard Urban |
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Affiliation: | Institut für Oganische Chemie, Technischen Universität, D-8000 München 2, Arcisstrasse 21, West Germany |
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Abstract: | The 1-ferrocenyl-2-methyl-1-propylamine (2a)is the most effective chiral template in asymmetrically induced peptide synthesis by stereoselective four component condensation (4CC). Two routes for the synthesis of this amine via its N,N-dimethyl derivative (12a) an described. One route involves the conversion of 12a into the corresponding azide 14a by treatment with methyl iodide/sodium azide in diglyme/water and subsequent reduction of the azide. The preferred other route consists of treating 12a with thioglycolic acid/formic acid to yield the carboxymethylmercapto derivative 9a and transformation of the latter into 2a with aqueous ammonia/ammonium chloride/mercuric chloride. Some related reactions are also discussed. |
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