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Practical Catalytic Enantioselective Synthesis of α,α-Dialkyl-α-amino Acids by Chiral Phase-Transfer Catalysis

Takashi Ooi, Mifune Takeuchi, Minoru Kameda and Keiji Maruoka

*Department of Chemistry, Graduate School of Science Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: maruoka.keiji.4wkyoto-u.ac.jp

T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc., 2000, 122, 5228-5229.

DOI: 10.1021/ja0007051


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Abstract

Structurally well-defined C2-symmetric chiral quaternary ammonium bromides catalyze a highly enantioselective solid-liquid phase transfer catalytic alkylation of aldimine Schiff bases of amino acid tert-butyl esters to provide a wide variety of α,α-dialkyl-α-amino acids.

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Practical Stereoselective Synthesis of β-Branched α-Amino Acids through Efficient Kinetic Resolution in the Phase-Transfer-Catalyzed Asymmetric Alkylations

T. Ooi, D. Kato, K. Inamura, K. Ohmatsu, K. Maruoka, Org. Lett., 2007, 9, 3945-3948.


Key Words

O'Donnell Amino Acid Synthesis, Organocatalysis


ID: J48-Y2000