Science of Synthesis

Terada, M., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 342.

Enecarbamates have been applied to the enantioselective ene reaction with azodicarboxylates as the ene component, and this reaction provides a novel route to various α-amination products.[‌114‌] For example, treatment of azodicarboxylates ‌77‌ with enecarbamates ‌78‌, using the chiral copper catalyst derived from copper(II) trifluoromethanesulfonate and the chiral 1,2-diamine ligand ‌79‌, gives the α-amino imines ‌80‌ with high levels of asymmetric induction (‌Scheme 28‌). The initially formed α-amino imines ‌80‌ can either be transformed into the ketones ‌81‌ upon acid hydrolysis or into the 1,2-diamines ‌82‌ by stereoselective reduction with sodium borohydride.

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References