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.Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.