94278-27-0Relevant articles and documents
REGIO- AND STEREOCONTROL IN THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION TO 2-FURYLTHIOL- AND 2-FURYLMETHANETHIOL DERIVATIVES.
Annunziata, Rita,Cinquini, Mauro,Cozzi, Franco,Raimondi, Laura,Licini, Giulia
, p. 3869 - 3886 (2007/10/02)
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.