Starting from the appropriate azides bearing the (S)-1-phenylethylamine and the l-alanine benzylester as chiral pendants, a facile and effective synthetic route to the title compounds in their enantiopure form was developed with excellent product yields obtained. Basic hydrolysis of the ester group of title compounds 3a–c gave the corresponding, readily functionalisable carboxylic acids. Catalytic reduction of 2-benzyl derivatives 3c and 3f gave 4-functionalised 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones in enantiopure forms.

A short synthesis of enantiopure 2-substituted 4,5-dihydro-1,4-benzodiazepin-3-ones via intramolecular azide cycloaddition / G. Molteni, P. Del Buttero. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 18:10(2007), pp. 1197-1201. [10.1016/j.tetasy.2007.05.015]

A short synthesis of enantiopure 2-substituted 4,5-dihydro-1,4-benzodiazepin-3-ones via intramolecular azide cycloaddition

G. Molteni;P. Del Buttero
2007

Abstract

Starting from the appropriate azides bearing the (S)-1-phenylethylamine and the l-alanine benzylester as chiral pendants, a facile and effective synthetic route to the title compounds in their enantiopure form was developed with excellent product yields obtained. Basic hydrolysis of the ester group of title compounds 3a–c gave the corresponding, readily functionalisable carboxylic acids. Catalytic reduction of 2-benzyl derivatives 3c and 3f gave 4-functionalised 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones in enantiopure forms.
alkenoyl aryl azides; potent; antagonists
Settore CHIM/06 - Chimica Organica
2007
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/43738
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