Resolution of nitrogen-centered chiral tetraalkylammonium salts: application to [1,2] Stevens rearrangements with N-to-C chirality transmission
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.
Tayama, Eiji,Otoyama, Seijun,Tanaka, Hiroyuki
experimental part
p. 2600 - 2608
(2010/03/24)
An efficient optical resolution of nitrogen-centered chiral β-hydroxy-tetraalkylammonium salts via complexation with (R)-BINOL
The optical resolution of nitrogen-centered chiral β-hydroxy-tetraalkylammonium bromides 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.
Tayama, Eiji,Tanaka, Hiroyuki
p. 4183 - 4185
(2008/02/05)
Synthesis of N-(dialkylaminoalkyl)alcohols by homogeneously catalyzed hydrogenolysis of cyclic N,O-acetals
The homogeneously catalyzed hydrogenation of 1,3-oxazolidines affording unsymmetrically substituted 2-N-(dialkylamino)ethanols is reported showing for the first time that Rh(I) catalysts based on chelating diphosphines can be advantageous for this reaction.
Tararov, Vitali I.,Kadyrov, Renat,Riermeier, Thomas H.,B?rner, Armin
p. 375 - 380
(2007/10/03)
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