85664-56-8Relevant articles and documents
Carbamoyl anion addition to nitrones
Reeves, Jonathan T.,Lorenc, Chris,Camara, Kaddy,Li, Zhibin,Lee, Heewon,Busacca, Carl A.,Senanayake, Chris H.
, p. 5895 - 5902 (2014/07/08)
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.
α-Oxygenation of Aldehydes and Cyclic Ketones by Acylation-Rearrangement of Nitrones
Cummins, Clark H.,Coates, Robert M.
, p. 2070 - 2076 (2007/10/02)
The reaction of N-tert-butylnitrones (1a-e) of aldehydes and N-methylnitrones (2 and 3) of cyclic ketones with acid chlorides in the presence of triethylamine afforded α-acyloxy imines by rearrangement of N-vinyl-O-acylhydroxylamine intermediates.Hydrolysis of the α-acyloxy imines gave α-acyloxy aldehydes and ketones.The acylation-rearrangement reaction offers a new method for α-oxygenation of carbonyl compounds.