Unusual reactivity of nitronates with an aryl alkyl carbonate: synthesis of α-amino esters.
The monoanions of nitroalkanes are ambident nucleophiles that react with carbonate electrophiles through the oxygen atom. Products arising from reactivity at the carbon atom will yield α-nitro esters, which are precursors for α-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where α-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to α-amino esters. This pathway could be a safe alternative to the Strecker reaction.
New Chemistry Unit and ‡International Centre for Materials Science, Jawaharlal Nehru Centre for Advanced Scientific Research , Bangalore 560064, India.
Golipalli Ramana
GR
Reddy
Debopreeti
D
Mukherjee
Arjun Kumar
AK
Chittoory
Sridhar
S
Rajaram