β-functional! Direct enantioselective amination of α-ketoesters with azodicarboxylates was demonstrated using an axially chiral guanidine base catalyst, which enabled efficient access to enantioenriched multifunctionalized ketoesters with an aliphatic substituent at the β-position. Subsequent nucleophilic addition to the β-hydrazinyl-α-ketoester at the reactive ketone yields the corresponding β-hydrazinyl-α-hydroxy esters in high syn diastereo- and enantioselectivities (see scheme).
If you can't find a tool you're looking for, please click the link at the top of the page to "Go to old article view". Alternatively, view our Knowledge Base articles for additional help. Your feedback is important to us, so please let us know if you have comments or ideas for improvement.