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

Abstract

An efficient synthesis of enantiomerically pure cyclohex-2-enols from the reaction of 2- p-tolylsulfinyl cyclohexanols with (CF 3CO) 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.