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Synfacts 2009(11): 1233-1233  
DOI: 10.1055/s-0029-1218128
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Phase-Transfer Catalytic Alkylation of Imidazoline-4-carboxylates

Contributor(s): Mark Lautens, Chit Tsui
Y. Park, S. Kang, Y. J. Lee, T.-S. Kim, B.-S. Jeong, H.-g. Park*, S.-s. Jew*
Seoul National University and Yeungnam University, Gyeongsan, Korea
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

α,β-Diamino acids are attractive synthetic targets due to their various biological ­activities. Most of the reported methods for their asymmetric syntheses involve the use of chiral substrates or chiral auxiliaries, which may limit their applications in large-scale industrial productions. The authors report herein a highly efficient and enantioselective method for the synthesis of (S)-α-alkyl-α,β-diaminopropionic acid 4 via asymmetric phase-transfer catalytic (PTC) α-alkylation of imidazoline-4-carboxylates 1.