REGIOCONTROL AND STEREOCONTROL IN THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION TO 2-FURYLTHIOL AND 2-FURYLMETHANETHIOL DERIVATIVES
Articolo
Data di Pubblicazione:
1991
Citazione:
REGIOCONTROL AND STEREOCONTROL IN THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION TO 2-FURYLTHIOL AND 2-FURYLMETHANETHIOL DERIVATIVES / R. ANNUNZIATA, M. CINQUINI, F. COZZI, L. RAIMONDI, G. LICINI. - In: TETRAHEDRON. - ISSN 0040-4020. - 47:23(1991), pp. 3869-3886. [10.1016/S0040-4020(01)80910-8]
Abstract:
A series of 2-furyl and 2-furylmethyl substituted nitrosulphides with a proper chain length were prepared and showed to undergo a totally regiocontrolled intramolecular furan-nitrile oxide cycloaddition to give cis-fused products in high yield. Insertion of a stereocenter on the cycloaddends did not allow satisfactory control of the absolute stereochemistry of the reaction. Enantiomerically enriched products (e.e. less-than-or-equal-to 95%) were obtained by a kinetic resolution process involving oxidation of the sulphide cycloadducts to the corresponding sulphoxides.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, G. Licini
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