Asymmetric synthesis of cyclohex-2-enols: The examples of seudenol and analogues

Article abstract of DOI:10.1016/0957-4166(95)00152-F

An efficient synthesis of enantiomerically pure cyclohex-2-enols from the reaction of 2-p-tolylsulfinyl cyclohexanols with (CF₃CO)₂O/Py and subsequent hydrogenolysis of the C-S bond with Li/Naphthalene, is reported. This strategy has been applied to the asymmetric synthesis of seudenol and 1-methylcyclohex-2-en-1-ol. New data on the rearrangement of the trifluoroacetate group when 2-p-tolylsulfinyl 1-methylcyclohexenols are treated under the Pummerer reaction conditions are also reported.