Chiral, multidentate sulfoxide ligands could have applications in coordination chemistry including catalysis.  To synthesize tetradentate aminosulfoxide ligands, the conjugate addition of various primary and secondary 1,2-diamines with either racemic or resolved p-tolyl vinyl sulfoxide has been extensively investigated.  Results of conjugate additions under two sets of conditions will be presented:  Use of neutral nucleophiles in protic solvents and use of diamide nucleophiles under aprotic conditions. With 1,2-cyclohexanediamine nucleophiles, the reaction is very sensitive to steric bulk at nitrogen as only N-methyl ligands may be synthesized by this route.  The possibility of kinetically resolving p-tolyl vinyl sulfoxide by this method will also be discussed.  Two literature methods for the asymmetric synthesis of p-tolyl vinyl sulfoxide have been explored and the utility of each method for large-scale synthesis will be compared. NMR, IR and chiroptical data on all new compounds will be presented.

Synthesis and characterization of single enantiomer tetradentate aminosulfoxide ligands

243rd National Meeting (2012)

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