Regio- and stereoselective ring opening of epoxides. Enantioselective synthesis of 2,3,4-trisubstituted five-membered heterocycles

By using the appropriate protecting groups, the opening of (2S,3S,4E)-5-benzenesulfonyl-2,3-epoxy-pent-4-en-1-ol (−)-2 could be controlled and used for the synthesis of the enantiomeric pyrrolidines (+)- and (−)-18 and the tetrahydrofuran analogs (+)- and (−)-19.