REGIO- AND STEREOCONTROL IN THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION TO 2-FURYLTHIOL- AND 2-FURYLMETHANETHIOL DERIVATIVES.

Article abstract of DOI:10.1016/S0040-4020(01)80910-8

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.