
Tetrahedron p. 3869 - 3886 (1991)
Update date:2022-07-31
Topics:
Annunziata, Rita
Cinquini, Mauro
Cozzi, Franco
Raimondi, Laura
Licini, Giulia
A series of 2-furyl and 2-furylmethyl substituted nitrosulphides with a proper chail length were prepared and showed to undergo a totally regiocontrolled intramolecular furan-nitrile oxide cycloaddition to give cis-fused products in high yields.Insertion of a stereocenter on the cycloaddends did not allow satisfactory control of the absolute stereochemistry of the reaction.Enantiomerically enriched products (e.e.=95percent) were obtained by a kinetic resolution process involving oxidation of the sulphide cycloadducts to the corresponding sulphoxides.
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