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.
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]
REGIOCONTROL AND STEREOCONTROL IN THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION TO 2-FURYLTHIOL AND 2-FURYLMETHANETHIOL DERIVATIVES
R. AnnunziataPrimo
;M. CinquiniSecondo
;F. Cozzi;L. RaimondiPenultimo
;
1991
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.Pubblicazioni consigliate
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