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Synlett 2009(4): 658-660  
DOI: 10.1055/s-0028-1087812
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© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids via Enantioselective Alkylation of Azlactones under Biphasic Conditions Using P-Spiro Chiral Tetraaminophosphonium Salts as a Phase-Transfer Catalyst

Daisuke Uraguchi, Yoshihiro Asai, Yuki Seto, Takashi Ooi*
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603 Japan
Fax: +81(52)7893338; e-Mail: tooi@apchem.nagoya-u.ac.jp;
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Publication History

Received 3 October 2008
Publication Date:
16 February 2009 (online)

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Abstract

Highly enantioselective alkylation of azlactones derived from α-amino acids has been achieved under solid-liquid phase-transfer conditions using P-spiro chiral tetraaminophosphonium salt as a catalyst. The resulting alkylated azlactones can be readily converted into the corresponding α,α-disubstituted α-amino acids through simple acidic hydrolysis.

Key words

aminophosphonium salt - phase-transfer catalysis - azlactone - α,α-disubstituted α-amino acid - asymmetric synthesis

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