http://www.cnr.it/ontology/cnr/individuo/prodotto/ID15111

Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines (Articolo in rivista)

Type

Label

Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines (Articolo in rivista) (literal)

Anno

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Alternative label

Schmidt A.; Marchetti M.; Eilbracht P. (2004)
Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines
in Tetrahedron (Oxf., Print)
(literal)

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Note

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Fachbereich Chemie, Organische Chemie I, Universitat Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund, Germany Istituto di Chimica Biomolecolare del C.N.R., Sezione di Sassari, Traversa La Crucca, 3 Località Baldinca, Li Punti, 07040 Sessari, Italy (literal)

Titolo

Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines (literal)

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. (literal)

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