Enantioselective synthesis amino acids, phase-transfer catalysis

Enantioselective Synthesis of Optically Pure Amino Acids Phase-Transfer Catalysis... 

Maruoka K, Ooi T (2003) Enantioselective amino acid synthesis by chiral phase-transfer catalysis. Chem Rev 103 3013-3028... 

Reviews on phase-transfer catalysis for the syntheses of a-amino acids, (a) Ooi, T. and Maruoka, K. (2004) Asymmetric organocatalysis of structurally well-defined chiral quaternary ammonium fluorides. Acc. Chem. Res., 37, 526-533 (b) Maruoka, K. and Ooi, T. (2003) Enantioselective amino acid synthesis by chiral phase-transfer catalysis. Chem. Rev., 103, 3013-3028 (c) Ooi, T. and Maruoka, K. (2003) Enantioselective synthesis of a-amino acids by chiral phase-transfer catalysis. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem.) 61, 1195-1206. 

Maruoka K, Ooi T. Enantioselective amino acid synthesis by chiral phase-transfer catalysts. Chem. Rev. 2003 103 3013-3028. O Donnell MJ. The enantioselective synthesis of a-amino acids by phase-transfer catalysis with achiral Schiff base esters. Acc. Chem. Res. 2004 37 506-517. 

Enantioselective synthesis of a-amino acids by phase-transfer catalysis with achiral Schiff base esters using Cinchona alkaloids as phase-transfer catalysts 04ACS506. 

Synthesis of amino acids from a Schiff base substrate of glycine, enantioselective alkylation by phase transfer catalysis (PTC) (see 1st edition). 

O Donnell MJ (2004) The Enantioselective Synthesis of a-Amino Acids by Phase-Transfer Catalysis with Achiral Schijf Base Esters. Acc Chem Res 37 506... 

Ooi, T., Takeuchi, M., Kameda, M., Maruoka, K. (2000). Practical catalytic enantioselective synthesis of a,a-dialkyl-a-amino acids by chiral phase-transfer catalysis. Journal of the American Chemical Society, 122, 5228-5229. 

Isovaline, one of the amino acids present in meteorites in enantioenriched form, catalyses the synthesis of tetroses with ee s up to 11% (44). This modest enantioselectivity is additionally hampered by the modest ee s of isovaline present in the meteorite. But as diseussed above, phase behaviour can provide for enantioenrichment in the solution phase and experiments showed that it ean indeed be coupled to chirahty transfer by catalysis in a single system. Enantiomerically pure L-serine for example eatalyses an aldol reaction wito 46% ee if it is used with only 1% ee and the reaction performed in equilibrium with a... 

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