Microwave-assisted ring expansion of N-acetyl 3′-unsubstituted aziridine in the presence of Lewis acids
The microwave-assisted ring expansion of N-acetyl 3′-unsubstituted aziridine-2-imides and N-acetyl 3′-unsubstituted aziridine-2-esters to oxazolines is reported. The regioselectivities of the rearrangements depend upon the reaction conditions, such as the Lewis acid selected and the solvent.
Cardillo,Gentilucci,Gianotti,Tolomelli
p. 2807 - 2812
(2007/10/03)
Ring expansion of N-acetyl aziridine-2-imides to oxazoline-4-imides, useful precursors of pure β-hydroxy α-aminoacids
Optically active N-acyl aziridine 2-imides or α-carboxylates rearrange to oxazoline-4-imides or 4-carboxylates with high regio and stereo control. This ring expansion followed by mild hydrolisis allows the synthesis of enantiomerically pure β-hydroxy α-aminoacid precursors.