Asymmetric catalytic nitrooxylation and azidation of β-keto amides/esters with hypervalent iodine reagents

Abstract

Chiral Lewis acid-catalyzed enantioselective nitrooxylation of cyclic and acyclic β-keto amides/esters with hypervalent iodine(III) reagents is reported. A number of α-nitrooxy-β-keto amides/esters were obtained with good yields and high enantioselectivities by using bench-stable nitratobenziodoxole under mild conditions. This methodology was also applied to azidation and produced α-azido-β-keto amides/esters with high enantioselectivities (up to 97% ee).