exo-Metallation of racemic 3-methyl-4,5-dihydroisoxazoles and reaction of the products with (-)-(S)-menthyl toluene-p-sulphinate afforded diastereoisomeric 3-sulphinylmethyl derivatives which can be separated and individually converted either into the corresponding enantio- and diastereoisomericaliy pure 4,5-dihydroisoxazoles or β-ketols, depending on the desulphurization conditions; furthermore, stereoselective reduction of the former provides an entry to optically active γ-amino alcohols.

Enantiomerically pure sulphinyl-4,5-dihydroisoxazoles. Part 1. Stereocontrolled synthesis of optically active β-ketols and γ-amino alcohols / R. Annunziata, M. Cinquini, F. Cozzi, A. Gilardi, A. Restelli. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :0(1985), pp. 2289-2292.

Enantiomerically pure sulphinyl-4,5-dihydroisoxazoles. Part 1. Stereocontrolled synthesis of optically active β-ketols and γ-amino alcohols

R. Annunziata;M. Cinquini;F. Cozzi;
1985

Abstract

exo-Metallation of racemic 3-methyl-4,5-dihydroisoxazoles and reaction of the products with (-)-(S)-menthyl toluene-p-sulphinate afforded diastereoisomeric 3-sulphinylmethyl derivatives which can be separated and individually converted either into the corresponding enantio- and diastereoisomericaliy pure 4,5-dihydroisoxazoles or β-ketols, depending on the desulphurization conditions; furthermore, stereoselective reduction of the former provides an entry to optically active γ-amino alcohols.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/185174
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