Enantioselective synthesis of imidazolines with quaternary stereocenters by organocatalytic reaction of N-(heteroarenesulfonyl)imines with isocyanoacetates |
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| Authors: | Nakamura Shuichi Maeno Yuri Ohara Mutsuyo Yamamura Akiko Funahashi Yasuhiro Shibata Norio |
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| Affiliation: | Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Nagoya 466-8555, Japan. snakamur@nitech.ac.jp |
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| Abstract: | An organocatalytic enantioselective Mannich-type reaction of isocyanoacetate with N-sulfonylimines catalyzed by chiral thioureas derived from quinine yielded 2-imidazolines with high diastereo- and enantioselectivities (up to >99:1 dr. and 96% ee). This reaction provided a convenient route to access various imidazolines and related α,β-diamino acids having a quaternary carbon center in high enantiomeric purities. |
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