Stereospecific benzyne-induced olefination from β-amino alcohols and its application to the total synthesis of (-)-1-deoxy-D-fructose

Article abstract of DOI:10.1002/chem.201001735

'Ole in one! Treatment of β-amino alcohols with CS₂ under alkaline conditions gave 1,3-thiazolidine-2-thiones, which were then treated with benzyne generated in situ. The reaction underwent an unprecedented addition-elimination process to give the desired olefins in 60-87 yields (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). Copyright