100054-98-6Relevant articles and documents
Resolution of nitrogen-centered chiral tetraalkylammonium salts: application to [1,2] Stevens rearrangements with N-to-C chirality transmission
Tayama, Eiji,Otoyama, Seijun,Tanaka, Hiroyuki
experimental part, p. 2600 - 2608 (2010/03/24)
The resolution of N-chiral, amino acid-derived quaternary ammonium salts is demonstrated by using chiral BINOL as a complexing agent. Determination of the enantiopurities and absolute configurations of the resolved N-chiral tetraalkylammonium salts are described. The [1,2] Stevens rearrangement of N-chiral ammonium salts is shown to proceed with N-to-C chirality transmission to afford optically active 3-substituted morpholin-2-one derivatives.
Reductive Cleavage of N-Substituted 2-Aryl-1,3-oxazolidines: Generation of α-Amino-Substituted Carbanions
Azzena, Ugo,Melloni, Giovanni,Nigra, Cristina
, p. 6707 - 6711 (2007/10/02)
The behavior of several N-substituted 2-aryl-1,3-oxazolidines has been investigated under conditions of electron transfer from alkali metals in aprotic solvents.The reduction led to the regioselective cleavage of the benzylic carbon-oxygen bond, with formation of the corresponding N-substituted benzylamino alcohols in good yields.Investigation of the mechanism of this reductive cleavage, with the aid of labeling experiments, showed the intermediate formation of α-tertiary amino-substituted carbanions.