Reactions of 2,5-dihydro-2,5-dimethoxy-furan with phenylselenenylchloride: Regio- and stereocontrolled generation of highly functionalized C4 building-blocks

Article abstract of DOI:10.1016/S0040-4020(97)10044-8

An efficient protocol for stereo- and regiocontrolled synthesis of small polyfunctional molecules is presented. The stereospecific addition of PhSeCl to 2,5-dihydro-2,5-dimethoxy-furan 1 in solvents, such as methylene chloride and methanol, gives cyclic and linear acetals 2 and 3, depending on the solvent used. Emphasis is given to the regiocontrolled hydrolysis of acetal groups for the preparation of stereodefined and highly functionalized C₄ synthons, such as 8, 9 and 13.