Carbamoyl anion addition to nitrones.

Jonathan T Reeves, Chris Lorenc, Kaddy Camara, Zhibin Li, Heewon Lee, Carl A Busacca, Chris H Senanayake

The Journal of organic chemistry 2014 Jun 20

filter terms:

The addition of carbamoyl anions derived from N,N-disubstituted formamides and LDA to N-tert-butyl nitrones is described. The reaction was demonstrated with a variety of formamides and nitrones and provided a direct route to α-(N-hydroxy)amino amides. The use of a tert-leucinol derived chiral auxiliary on the nitrone provided products in good diastereoselectivity. Derivatization of the products by tert-butyl deprotection or N-deoxygenation was demonstrated.

Citation

Jonathan T Reeves, Chris Lorenc, Kaddy Camara, Zhibin Li, Heewon Lee, Carl A Busacca, Chris H Senanayake. Carbamoyl anion addition to nitrones. The Journal of organic chemistry. 2014 Jun 20;79(12):5895-902