Nagase α,α-disubstituted Amino Acids

By: Matthias Junkers, Aldrich ChemFiles 2008, 8.7, 7.

Aldrich ChemFiles 2008, 8.7, 7.

Chiral quaternary ammonium catalysts can be particularly useful in the field of asymmetric synthesis. Keji Maruoka and co-workers from Kyoto University have reported potent C2-symmetric ammonium salts that catalyze alkylation reactions under remarkably low catalyst loadings.1 Nagase, in close cooperation with Prof. Maruoka has applied his methodology in industrially viable procedures to synthesize α−monosubstituted and novel α,α-disubstituted α−amino acids by alkylation of alanine- (Scheme 1) and glycine-derived (Scheme 2) Schiff bases with alkyl halides. Research quantities of novel Nagase α,α-disubstituted amino acids are now available through Sigma-Aldrich®. Enantiopure allylalanines for example will open pathways to completely new structures. Rutjes and co-workers have already shown that the comparable allylglycine is a remarkable precursor for the synthesis of a broad range of building blocks.2

Scheme 1

Scheme 2

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  1. (a) Kitamura, M. et al. Angew. Chem. Int. Ed. 2005, 44, 1549. (b) Ooi, T.; Maruoka, K. Aldrichimica Acta 2007, 40, 77.
  2. (a) Rutjes, F.P.J.T. et al. J. Org. Biol. Chem. 2005, 3, 3435. (b) Rutjes, F.P.J.T. et al. J. Chem. Soc., Perkin Trans. 1 2000, 4197.

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