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
LICINI, GIULIA MARINA
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.
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