Tetrahedron: Asymmetry

Resolution of nitrogen-centered chiral tetraalkylammonium salts: application to [1, 2] Stevens rearrangements with N-to-C chirality transmission

E Tayama, S Otoyama, H Tanaka

Index: Tayama, Eiji; Otoyama, Seijun; Tanaka, Hiroyuki Tetrahedron Asymmetry, 2009 , vol. 20, # 22 p. 2600 - 2608

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Citation Number: 12

Abstract

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.