Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines |
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Authors: | Andreas Schmidt Peter Eilbracht |
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Affiliation: | a Fachbereich Chemie, Organische Chemie I, Universität Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund, Germany b Instituto di Chimica Biomoleculare del C.N.R., Sezione di Sassari, Traversa La Crucca, 3 Località Baldinca, Li Punti, 07040 Sessari, Italy |
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Abstract: | Pharmacologically active 4,4-diarylbutylamines like Fluspirilene and 4-amino-1,1-diarylbutan-1-ols like Difenidol were prepared in high yields via rhodium catalysed hydroaminomethylation of 1,1-diaryl-allylalcohols. Conversion of these olefins with carbon monoxide, hydrogen and secondary amines proceeds with complete regioselectivity. This group can easily be removed under acidic and hydrogenating conditions, enabling the transformation of 4-amino-1,1-diarylbutan-1-ols to 4,4-diarylbutylamines in high yields. Thus Fluspirilene was synthesised in 88% yield in four steps starting from commercially available materials. |
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Keywords: | Hydroformylation Hydroaminomethylation Rhodium Homogeneous catalysis |
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