STEREOCONTROL IN RADICAL CYCLIZATION: STEREOSELECTIVE SYNTHESIS OF 2,4-CIS AND 2,4-TRANS TETRAHYDROFURAN DERIVATIVES VIA MONO- OR DICHLOROMETHYL RADICAL.

Article abstract of DOI:10.1016/S0040-4039(00)80085-4

A novel stereocontrol method for the preparation of 2,4-disubstituted tetrahydrofurans was presented. 2,4-Cis-disubstituted-3,3-dichlorotetrahydrofurans 2 were provided predominantly by the radical cyclization of allyl-2,2,2-trichloroethylethers 1 with tributyltin hydride.The effect of geometry of chlorine atom and olefin on products stereochemistry was also discussed.