Reaction of stereoisomerically pure sulphinyl-4,5-dihydroisoxazoles having one or two stereocentres at C-4 and C-5 of the heterocycle with aliphatic or aromatic aldehydes resulted in highly stereoselective formal double aldol condensation; the adducts, depending on desulphurization conditions, could be converted either into optically active ββ′-dihydroxy ketones (by Raney nickel catalyzed hydrogenation in the presence of boric acid) or hydroxyisoxazolines (by Na-Hg in buffered conditions); the latter have the heterocyclic ring available for further synthetic elaboration such as highly stereoselective lithium aluminium hydride reduction to amino diols.

Enantiomerically pure sulphinyl-4,5-dihydroisoxazoles. Part 2. Synthesis of masked and unmasked β,β′-dihydroxy ketones via stereocontrolled double aldol condensation / R. Annunziata, M. Cinquini, F. Cozzi, A. Restelli. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 1985:11(1985), pp. 2293-2297.

Enantiomerically pure sulphinyl-4,5-dihydroisoxazoles. Part 2. Synthesis of masked and unmasked β,β′-dihydroxy ketones via stereocontrolled double aldol condensation

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

Abstract

Reaction of stereoisomerically pure sulphinyl-4,5-dihydroisoxazoles having one or two stereocentres at C-4 and C-5 of the heterocycle with aliphatic or aromatic aldehydes resulted in highly stereoselective formal double aldol condensation; the adducts, depending on desulphurization conditions, could be converted either into optically active ββ′-dihydroxy ketones (by Raney nickel catalyzed hydrogenation in the presence of boric acid) or hydroxyisoxazolines (by Na-Hg in buffered conditions); the latter have the heterocyclic ring available for further synthetic elaboration such as highly stereoselective lithium aluminium hydride reduction to amino diols.
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/2434/185183
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