Lewis Acid Catalyzed Condensation between Glycine Iminoester Enolates and p-Tolylsulfinimines

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Abstract
In the presence of Lewis acids, p-tolylsulfinimines react with glycine iminoester enolates to produce, after cyclization of open-chain intermediates, enantiopure N-sulfinylimidazolidines with good stereoselectivity. The predominant facial outcome of the process is opposite to most known examples involving enolates and sulfinimines. Two of these adducts have been easily transformed into novel non-symmetrical differentially protected vicinal diamines.

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